Style 101 – One-Hour Emergency Fashion Course

The foundations of style delivered to you in one hour with an exam to test your knowledge about the subject matter. 

Lesson 1: Your Style Priorities (5-7 minute read)
Lesson 2: Shopping For Your Body Type (5-7 minute read)
Lesson 3: The Wardrobe Necessities (5-7 minute read
Lesson 4: The Do’s And Don’ts Of Wearing A Suit (7-9 minute read)
Lesson 5:The Difference Between Sports Jacket, Suit Jacket And A Blazer  (6-8 minute read)
Lesson 6: A Brief Guide To Shirts (5-7 minute read)
Lesson 7: Understanding Trousers (5-7 minute read)
Lesson 8: Shoes And Accessories (8-10 minute read)
Lesson 9: Coats And Outerwear (5-7 minute read)
Lesson 10: Dress Standards And Dressing Well For All Events (3-5 minute read)


Lesson 1: Your Style Priorities





young-man-dressing-sharp-blue-jacketWhat’s important and what’s not. The best way to look well-dressed is to only own clothes that look great on you!

Building that entirely well-suited wardrobe is a challenge of priorities. It means understanding what’s important in your clothing — and what’s not. Think of it as a cost/benefit exercise.

Every item you buy has a price, and it has certain features and characteristics.

The goal is to only buy ones where those characteristics are so flattering to you that they’re worth the price. So what to look for?


Top Priorities – What Matters

rightvswrong011. Fit

This is number one and it’ll always be number one. A good fit is a top requirement for every single piece of clothing you own, from a custom suit on down to your underwear.

It’s a triage point: something that doesn’t fit perfectly is something you don’t need to buy.

There’s room for adjustments, of course. There’s nothing wrong with buying a second-hand jacket that’s a little long in the sleeves. You can always have those taken in. But in general, don’t bother with things that don’t already fit you.

What does a good fit mean? In general, every piece of clothing should:

  • sit close to the body, with no billowing or sagging
  • move with you without pinching or wrinkling at tight spots
  • be the appropriate length (sleeves all the way to wrists, etc.)

If you’ve got big flapping excess stretches of cloth, pinching at the joints or waist, or sleeves/legs that come up short or hang too long, skip it!

A good fit is what makes your clothes have that “sharp” look.

It can’t be imitated by anything that’s not fitted right. That’s why this is, and will always be, the number one important factor in menswear.


12888734325_7191b28b4b_o2. Fabric

The difference between a $100 suit and a $1000 suit mostly comes from two factors: the skill and detail of the tailoring, and the quality of the cloth. There’s no substitute for the real thing.

A fine worsted wool suit drapes in a way that a synthetic blend can’t and  a 100% cotton dress shirt presses to a sharp-edged crispness that  something thinner and cheaper won’t. Materials matter.

They matter a lot, more than anything else but the fit. If a garment looks cheap or feels flimsy — skip it! It’s not worth the investment, even if the cost is low. It’s making you look cheap when you wear it, and why would you ever pay for that?

In general, the “gold standard” for clothing is 100% wool for suits and 100% cotton for dress shirts.

You can tell a good cloth by its weight and “hand feel” — how smooth and lustrous it feels to the touch. Be wary of anything that’s artificially slick or unpleasantly coarse. Remember, you’ll be wearing it.

12860137893_43d07f1766_z3. Style

There are two key questions you need to ask about the style of every garment you ask:

  1. Does this work with the rest of my wardrobe?
  2. Will this work with my wardrobe ten years from now?

If the answer to either one of those is “no,” you might want to rethink the garment. A classic, timeless style is worth serious investment. But it needs to be a style that will last through both your tastes and other people’s.

You don’t have to be completely conservative — just ask yourself those two questions, and answer honestly.

The best suit in the world doesn’t do you much good if you don’t have anything to wear it with, or if you’re going to feel silly wearing it more than once or twice.

Low Style Priorities — What Doesn’t Matter

olive-green-suit1. Trendy

A “trend” is, by definition, something that isn’t going to last. That makes it a pretty dubious thing to spend money on. Part of the fashion industry is a never-ending cycle of “new looks,” most of which are just quirky alterations on the same basic styles.

After all, a good suit or shirt can last a man upward of a decade, if he takes good care of it, but clothing companies need you buying new garments much more frequently than that. So there’s a lot of artificial pressure to make things “hopelessly outdated” as soon as possible.

The way out of that trap is to buy things that are timeless, not trendy. Look for clothes that will look natural on you — and that would have looked natural on your father — and that would have looked natural on his father.

Chasing the latest trend just means having to buy new clothes when it’s not the latest trend anymore.

And often you also end up looking flat-out silly — think of the huge lapels and shoulder pads of the 1980s. Did anyone really look good in those? No. But “trendy” people still wore them, and that was their mistake.

12843263045_7f1f1dffe4_m2. Designer Labels

In theory, “designer” labels can charge more than other clothiers because the designer has already “proven” him or herself. The idea is that they’re an established fashion presence, and you can buy with confidence because they’re guaranteed to be in style.

The trouble with that theory is that major labels put out major mistakes from time to time, while the nameless designers behind more generic labels can make perfectly good clothing. The other problem is that big-name designers cost their employers money.

You pay more for the clothing, and less of that cost is going toward the quality — it’s going to the design, instead, and sometimes the savings come out of the material.

If you’re going to pay $250 for a pair of jeans, or $2500 for a suit, you want it to be something that will last you for years and always be in style, not something flimsy that will very briefly be a hot item because it came from a well-known brand name.


budget02Conclusion: Spend Your Money Wisely

Every clothing purchase is a game: you’re trying to get the most benefits for yourself at the lowest dollar price possible.

You do that by refusing to buy anything that doesn’t bring a major benefit to the table.

And as tempting as other things might be, there’s really only three things that you want to demand from everything you buy:

Fit — perfect for you at every point

Fabric — thick, sturdy, and well-constructed

Style — timeless, classic, versatile, and in tune with your existing wardrobe

Anything else just isn’t a high priority.


Click here to watch this unlisted video as I explain the importance of the Style Pyramid.

The Style Pyramid



Lesson 2: Shopping For Your Body Type






Shopping for your bodyGetting the right clothes for the right man. If you read Lesson One, you already know that the most important aspect of your clothing is the fit. And if you skipped Lesson One, we’re telling you now: fit is the most important aspect of your clothing. Period. No exceptions.

That means the most valuable thing you, as your clothing-purchaser, can do is make sure the clothes are well-suited to your body.

To really take your clothes to the next level, that means not only knowing your measurements and getting a good tailored fit but also buying clothes that flatter your particular complexion and build.





CasualShop Smart: How to Purchase for Your Body

Whenever you buy clothes, triage your choices in this order:

1.PHYSICAL LIMITS: What fits and flatters my body?

2.NEEDS: What meets my professional and practical needs?

3.WANTS: What has a style that I personally enjoy?

There’s no reason to buy a jacket in a style you like if you have nowhere to wear it, and there’s no reason to buy a good suit that meets your professional needs if it’s going to look bad on your body.

That’s why you take your physical limits, your needs, and your wants in order.

So how do you meet the physical needs? Think about three basic characteristics and then dress for those:

  • Your color and complexion
  • Your height
  • Your width and weight

If you’ve got an item that works well with all three of those characteristics, give it a passing grade on the physical limits, and start thinking about whether it meets your needs and wants.


Color and Contrast

You can get very abstract with color theory if you want to, but for most men’s practical purposes it comes down to the idea of contrast.
Contrast describes the change from one color to another color laid side-by-side with it — in fashion, usually either the colors of two pieces of clothing, or a piece of clothing and your bare skin.

Broadly speaking, men can be divided up into high-contrast, low contrast, and medium-contrast complexions:

  • High contrast men have significant differences in their hair, skin, and eye colors. A light-skinned man with dark hair has a high-contrast complexion, as does a dark-skinned man whose hair has turned white with age.

  • Low-contrast men have very little change from their skin color to their hair or eye color. A dark-skinned man with black hair and brown eyes is low-contrast, as is a blonde-haired, blue-eyed, fair-skinned man.

  • Medium-contrast men have complexions with colors that vary, but are not vividly contrasting. A freckled redhead with green eyes has contrast, but it’s not sharp contrast, making him a medium-complexion man; the same goes for an olive-skinned brunette with hazel eyes.


Whatever your complexion, you always want to roughly mimic the amount of contrast in it with the same amount of contrast in your clothes. Thus, a low-contrast man should wear outfits made mostly of similar colors, with only a few accent pieces that stand out.

High-contrast men, on the other hand, do well when each piece of clothing has a clear contrast with its fellows. One example is a low-contrast African-American gentleman with dark hair, dark skin, and dark eyes would look good in a matched suit and a slightly lighter but still dark-shaded shirt.

The same suit would look awkward on a tanned man with light hair and blue eyes — he needs a lighter shirt to contrast with the dark suit.




Dressing for your height is all about normalization. A tall man wants to avoid looming; a short man wants to avoid looking stubby. Men in the middle want to avoid extremes.

Visual impressions of height come mostly from the way our eye travels up the body. If our gaze tends naturally upward, sweeping quickly toward the face, it gives an impression of height.

If our gaze lingers instead on the midsection, without being guided upward, we perceive a shorter person. Men of different heights should use the eye’s natural progression to their advantage:

Short men want as clean and uncluttered a style as possible, to keep the eye from lingering on their midsection. They look best in smooth, untextured cloth, solid colors, and vertical-oriented stripes, all of which help guide the eye upward.

They also should avoid unnecessary detailing like pocket flaps, monograms, and large belt buckles, which keep the eye focused on the middle of the body.

Tall men, in contrast, look best when they have a busier style. Textured cloth, horizontally-oriented patterns like checks, and personal details like patterned pocket squares and brogued shoes help keep them from looking too looming.

Average men who are neither tall nor short want to avoid an excess of clutter and     horizontal elements (which will make them look stouter), but they don’t need the perfectly clean up-and-down of a short man’s outfit. Light textures and restrained patterns help an average man stand out without distorting his figure.

None of these are hard and fast rules — a tall man can look good in pinstripes, if he’s sensible about the other items in his wardrobe, and a short man can wear plaid. But in general, dress to guide people’s eyes the way that flatters you best: swiftly up and down for shorter men, and lingering lower on the body for tall men.



fatman01Width and Weight

These are not quite the same thing, and of the two width is the important one. Your weight doesn’t affect the fit of your clothing; the circumference of your body at various points does. That said, clothing can certainly affect how heavy you look, and men who want to look more or less full-figured can use that to their advantage:

  • Heavyset men who want a slimmer appearance should wear a jacket whenever possible. A plain, dark jacket and a plain, light shirt makes a narrow “V” on the front of the body that slims the whole appearance down.
  • A close fit with no sagging cloth also makes the figure look more trim, and a clean style with few visual details helps the eye travel quickly on up to the face, minimizing the impact of the body’s width.
  • Slim men can look a bit more filled-out by wearing a slightly looser fit (still no sag, however — there should never be loose, flapping cloth) and heavier, textured fabrics. Horizontally-oriented patterns add the illusion of breadth, and a wide jacket spread makes the chest look broader.
  • Average men shouldn’t try to slim down or bulk up — they can wear most patterns, colors, and fabrics naturally. The only key things to avoid are extremes, of either very bulky and textured fabrics (like a heavy-weight tweed) or very light and breezy fabrics (like an ultra-fine linen).

These style choices are a bit less forgiving than those for height. A bulky, rounded man is always going to look less than his best in a thick jacket with a checkered pattern.

Put the same man in a slim, dark gray jacket with a clean white shirt, and suddenly he looks powerful and imposing rather than round.


Conclusion: Your Body Comes First

All your wardrobe pieces should suit your body, your needs, and your wants. But of those three, the body comes first.

Vet every considered purchase for all three major characteristics of your physical form:

  • Color and complexion
  • Height
  • Weight

If it suits all three, you might have a winner. Start thinking about whether the piece meets your professional and personal needs.

Dress sharp for less? Click here to watch the video.





Lesson 3: The Wardrobe Necessities





Items that every man should own, regardless of his job or tastes. This one’s an easy lesson: it’s the essentials.

These are the pieces of clothing that every man will have a use for. Obviously, some are “higher status” than others — a business suit in particular — but even a working class man will occasionally need a business level of formality, even if it’s only for weddings or (if he’s unlucky) court dates.

closet101So if you don’t have all of these in your closet already, start filling the gaps:

  • 1 solid, dark, single-breasted business suit
  • 1 blue or gray blazer or sports jacket
  • 1 plain white dress shirt
  • 2-3 lightly-patterned or light-colored dress shirts
  • 1-2 light blue button-down work shirts
  • 1 pair dark dress slacks (wool or cotton)
  • 1 pair light cotton slacks (khakis, etc.)
  • 1 pair dark, fitted blue jeans
  • 1 pair plain black leather dress shoes
  • 1 black leather belt
  • 2-3 conservatively patterned neckties
  • 2-3 pocket squares
  • socks and underwear

Just those would make a pretty sparse wardrobe — you’d be doing laundry every couple of days to stay in clothing. This is, once again, a list of the bare necessities. Expand on it — but be sure to have each of these. A little more detail on each one:

  • The Business Suit: This is “the interview suit,” “the wedding suit,” and basically the go-to for any other event where you have to look absolutely top-notch. It should be either charcoal gray, navy blue, or black, without patterning or visible texture. A single-breasted, two-button jacket is the simplest and most versatile style.
  • dressing-sharp-for-one-week-with-only-13-items-750

    Click on the image for a larger view of the infographic

    The Blazer: A navy blue blazer is always reliable, but a man who prefers a more casual jacket could wear medium gray or dark brown in basically the same situations. More than one sports jacket is useful, but have at least one simple, solid one in the closet.

  • The White Dress Shirt: Plain white, with a point or spread (not button-down) collar. This is what you wear with the business suit when you want to look as dressy as possible. Keep it well-pressed and bleached to a nice clean white.
  • The Other Dress Shirts: For most business purposes you can wear a lightly-patterned shirt or one in a light, pastel solid instead of plain white. Have a selection so that you’re not always wearing the same thing.
  • The Work Shirts: A tough blue oxford shirt is a working class staple (it’s where we get “blue collar” from) and something every guy can find a use for. Wear it with jeans and a blazer and you’ve got an all-occasion dress-casual look; lose the jacket and you’re ready for physical labor.
  • The Dark Slacks: Gray wool flannel is ideal here, but you can get away with gray or navy blue cotton if you prefer. For occasions where a suit is too strict and jeans or khakis are too casual.
  • The Light Slacks: Khakis, for most of us, though light brown or olive fill the same role. For summer dress and very relaxed business situations.
  • The Jeans: Dark indigo, not light blue, and fitted reasonably close to the body. These are for looking casual but good, not for doing construction work in. Yellow, orange, or white contrast stitching is fine so long as it’s minimal (no knotwork on the butt pockets, guys).
  • The Dress Shoes: If you’re only going to own one pair, it should be plain black oxford balmorals. You can wear them with your suit, or with slacks and a jacket. Ideally, own the black dress shoes and then a few more casual pairs of leather shoes, but start with plain black.
  • The Belt: Plain black leather to go with your plain black shoes, with a small, slim, metal buckle.
  • The Neckties: Your first few should be simple and dark-colored — think burgundy, royal blue, hunter green, etc. Minor patterning is fine, so long as it’s not too ostentatious.
  • The Pocket Squares: It sounds like an optional item to some men, but if you’re wearing a jacket you really should have a pocket square in it. Have one white one that you can fold crisply for your most formal occasions, and a few colored/patterned ones for casual wear.
  • Socks and Underwear: The simplest way to wear socks is matched to the color of the trousers, so try to buy with your selection of pants in mind. Have a few pairs for each color of trousers in your wardrobe. Underwear is best left to your personal preference — but it’s not an option.

If you have all those things, you can appear at basically any event. At your most formal, you’ll be wearing a dark business suit, a white dress shirt, black shoes, socks, and belt, and a conservative tie with a white pocket square.

At your most casual, you’ll be in jeans and a button-down work shirt. And those are a pretty good set of benchmarks to bracket the vast majority of your wardrobe. Add a tuxedo or some grubby T-shirts if your life needs them, but they’re just not mainstays for most of us (or they shouldn’t be, anyway).



How many outfits can you get from 14 clothing items? Click here to watch the video.






Lesson 4: The Do’s and Don’ts of Wearing a Suit






dae3366e6f0da272f81271e384f0a06fThe pinnacle of sharp dressing — how to wear a man’s suit right.  The suit is the quintessential piece of menswear. The basic idea of a matched jacket and trousers has influenced almost every other item that we wear, in one way or another.

For all that, suits aren’t something that most men wear day to day anymore. Outside of high-status industries like finance and law, suits are considered too formal for work wear, and few men see them as a casual wear option (although they can be).

There are, broadly speaking, three ways to wear a men’s suit:

  • as traditional businesswear
  • as a personal style for social wear
  • as formalwear

 13275790945_9b63e69449_kThe Suit as Business Dress

A business suit is a fairly strict interpretation of the style. At its strictest, it can only be worn in certain colors and with certain accents:

  • dark, solid-colored jackets and trousers
  • plain white dress shirt
  • black leather shoes and belt
  • white pocket square
  • dark, conservative necktie

For most men’s practical purposes, there’s actually a little more flexibility than that — in industries where you’re wearing a suit every day, people need a little variety, and so we get things like the dark suit with fine white pinstripes or the gray Glen check.

But in general, when you talk about a business suit, you’re talking about something in dark wool that’s worn with a white dress shirt and a necktie.

Business suits can be single-breasted, double-breasted, or three-piece (single-breasted with a matching waistcoat). Both notch and peak styles of lapels are appropriate. They usually have minimal detailing: no pocket flaps, no trouser cuffs, etc.



12842887145_212a96652d_oThe Suit as Social Dress

It’s becoming something of a lost art, but the casual suit is still a viable option for men who want to look well-dressed without looking stuffy. Some business suits can be worn casually simply by taking off the necktie or wearing a colored shirt instead of a white one.

However, the best casual suits are visibly distinct from anything you would wear to the office as a work outfit:

  • lighter colors
  • visible patterns
  • textured fabrics
  • “busier” styles — flap pockets, added ticket pockets, etc.

At the extreme end, this can lead to fashion statements like exaggerated lapels or extra-long jackets (think zoot suits), but there’s no need to go that far. A light plaid or brown corduroy suit, worn with an open-collared shirt (or even a non-collared one), makes it clear that you’re not going into the office.

Depending on its styling, a casual suit can be a good choice for concerts, dance clubs, theater, and fine dining. It’s also a traditional choice for church services, though hardly the norm these days. There’s no situation where one would ever be considered mandatory, however, making a casual suit purely a personal style choice.




Click on the image for a larger view of the infographic

The Suit as Formal Wear

When we say “tuxedo,” we’re usually talking about the whole black tie ensemble, which would be more properly called a “dinner suit.”

The dinner suit and other styles of formal and semiformal wear (strollers, morning coats, etc.) are fancier and in some cases older versions of the traditional men’s suit, and they all follow very specific rules.

For the most part, you will only need to worry about these when you’re invited to a formal event, and even then many people aren’t following the full set of rules (tuxedos at daytime weddings, for example, is technically improper use, but plenty of people do it anyway).

Most men solve formal dress situations with rentals, which is fine so long as you’re careful about who you rent from and make sure to do a bit of reading on true black tie standards beforehand.

It’s also worth noting that a plain, dark business suit can stand in for formalwear at a “black tie optional” event.

It’s the only alternative that’s appropriate, and should be worn at maximum business formality (plain white shirt, plain black shoes, etc.), but that’s the meaning of a black tie optional invitation, and it’s a good option for men who have reason to own a business suit but no need to own a tuxedo.


Conclusion: The Suit in Your Wardrobe

Some men will own one suit in their lives and some will own dozens. It has a lot to do with professional necessity and, in some cases, a little to do with personal taste.

A plain, dark-colored, single-breasted business suit is pretty much always worth having in the closet, for special occasions and high-stakes moments like job interviews if nothing else.

Beyond that, expand the selection if you’re in a suit-and-tie business, or if you’re someone who likes wearing suits as part of his personal style. In either case, add a variety of cuts and styles so that things don’t get too repetitive.

What is the difference between a suit and a tuxedo? Click here to watch the video.





Lesson 5: The Difference Between Sports Jacket, Suit Jacket And A Blazer






The most useful and versatile piece of men’s clothing: the unmatched jacket. The matched suit is the most formal of men’s wardrobe choices, short of true formalwear like tuxedos and morning dress, but the unmatched jacket is the most versatile.
Sports jackets, blazers, and even the occasional suit jacket worn without its matching trousers can meet almost any standard of dress.

They can pair with good slacks and a necktie for business wear, or they can go with jeans and a pair of canvas sneakers and fit right in at a rock concert. It’s all in how you wear it. While they’re all similar, it is worth knowing the differences between blazers, sports jackets, and suit jackets:

  • 12882529213_63afa646dc_kBlazers are wool, usually a smooth worsted weave, and are dressier than sports jackets. The iconic style is the navy blue blazer with metallic (usually brass) buttons, and it’s a good example of the characteristics: a little stiffness and structure in the tailoring, large patch pockets; double- or single-breasted. Most are solid-colored, though there are patterned blazers out there, particularly light plaids.
  • Sports jackets, also sometimes called sportcoats, are less dressy than blazers. They’re descended from rural British outdoorswear, and tend to come in textured fabrics like tweed or corduroy. Casual colors and patterns are both common. The shape is usually softer and less shaped than a blazer, and they often have casual accents like pocket flaps and elbow patches.
  • Suit jackets are the upper half of a matched suit, and tend to be made from a finer wool than either blazers or sports jackets. The pockets are usually simple slits, and the cut is sharper and more shaped. Single-breasted, two-button versions can be worn with jeans for deliberate contrast, but mostly they’re only meant to be worn with their matching trousers.

The lines between the three often get blurred, particularly between blazers and sports jackets, so be ready to use both words when shopping. You can find rugged, tweedy jackets billed as “blazers,” and dressy, preppy blazers called “sportcoats.” In general, though, blazers are the boxier, dressier style, and sports jackets are softer and more casual.



Jackets for Business Wear

For most of us, suits aren’t day-to-day business wear. That’s too bad, because suits are sharp-looking pieces of clothing. Happily, you can get the same basic benefits from wearing a jacket, making it an ideal business-casual option for most men.


Click on the image for a larger view of the infographic

The jacket emphasizes the shoulders and slims the waist, giving you a “sexier” silhouette, and it’s a clear gesture that you’re going out of your way to look “dressed up” for work. Blazers are typical business-casual wear, particularly navy blazers with either khakis or gray slacks.

People who want a more relaxed look, like teachers and artists, usually do better in a sports jacket. Either one can be worn with or without a tie; the tie obviously makes the outfit dressier and more formal. For a good idea of the variety you can get, think about two different work-appropriate outfits:

  • A navy blue blazer worn with khakis, a white shirt with light blue checks, a colored necktie, and black leather dress shoes with a matching belt — this is just shy of a suit’s formality, and appopriate for reasonably high-formality meetings and offices.
  • A soft-shouldered brown corduroy sportcoat worn with blue jeans, an open-collared blue-and-white candystripe shirt, and brown saddle shoes with a brown belt and decorative metal belt buckle — this would never pass muster in a conservative business office, but it would look great for a software engineer in a relaxed office or a teacher at an elementary school.

Both are jackets worn for work, but they’re completely different — which is part of why you may want several jackets in your wardrobe, ranging in style from conservative blazers to funky and off-beat jackets.


Jackets for Social Wear

You can also use both blazers and sports jackets for social dress, although blazers are less common (unless you belong to a yacht or country club). In nearly all cases you won’t wear a necktie with a jacket when you’re off-duty.

The combination of a traditional, lapeled jacket with a necktie just reads as “business dress” in the modern fashion language. That’s not to say that there aren’t fashionable looks using both neckties and jackets, but they’re not common, and you need a good instinct for style to pull it off without looking like you just came from the office.

So for the most part, wear your jackets with an open collar, or with a non-collared shirt. Everything from dress shirts without neckties on down to colored T-shirts can be worn under a jacket, for a variety of looks. Again, consider two contrasting examples:

  • A light gray tweet jacket worn with a light blue, open-collared dress shirt, a pair of dark gray flannel trousers, black loafers with silver buckles, and a matching black belt — you could wear this to a conservative church or a “linen tablecloth” restaurant and fit right in, but it’s still casual enough that you could go to the local pub for a drink as well.
  • A light gray canvas or cotton twill jacket with big patch pockets, cut long and loose, with a black T-shirt underneath, fitted jeans, and a pair of red Converse All-Stars — this could go to a rock concert or dance club, or to the latest and trendiest of food spots in a big city.

What you wear the jacket with matters almost as much as the style of the jacket, for social purposes. Play around and experiment with different looks — the shape of the traditional men’s jacket is always going to be working in your favor, and you’ll stand out from all the men in their shirtsleeves.



Conclusion: The Jacket in Your Wardrobe

In short, the basic men’s jacket, whether it’s a sports jacket, a blazer, or even a dark suit jacket worn with different trousers, deserves its place as a mainstay of the stylish man’s wardrobe.

Build your collection slowly with an eye to quality and variety. A traditional navy blazer is never a bad starting place, but there’s plenty of room in everyone’s style for more relaxed blazers and sport coats as well.


Are blazer jackets and sports jackets interchangeable? Click here to watch the video.






Lesson 6: A Brief Guide to Dress Shirts






How to always have the right shirt for your outfit. Men’s shirts lack the glamour of suits and jackets, but they’re no less vital to your personal style.

The difference between a plain white dress shirt and a light blue one can be enormous, in the right context — and, for that matter, so can the difference between a white dress shirt with a wide spread collar and one with a narrow collar.


ledbury-ties-e1447152429405Dress Shirts: Men’s Business Shirts

“Business” is somewhat misleading when applied to shirts — there are plenty of occasions where a man might wear an office-appropriate shirt to a social event.

They’re much less rigidly divided than suits in that respect. But for the most part, the phrase “dress shirt” refers to a basic style of shirt that’s remained a largely-unchanged staple of the male wardrobe for the better part of a century:

  • made from finely-woven cotton, cotton blend, or synthetic material
  • long-sleeved
  • button-fronted
  • turndown collar

The shirt is generally symmetrical, apart from an optional pocket on the left breast, and the patterns on shirts meant for business wear will usually be minimal, white-based, and symmetrical as well, though occasional exceptions do exist.




Click on the image for a larger view of the infographic

Collar Styles

Among more conservative, business-oriented dress shirts, the collar is one of the more distinctive features. Collars come in a couple different styles:

Point collar: This is the most common style, in which the collar points simply lie flat on the shirt front.There are no buttons or fasteners of any kind, apart from one top button above the other shirtfront buttons that closes the very top of the shirt.

Spread collar: A spread collar is exactly like a point collar, but with a wider “spread” or angle between the collar points. Typically, if the two points of the collar are offset by more than 90 degrees (a right angle) it’s considered a spread collar. In many cases, spread collars are also shorter, with less cloth “turned down.”

Button-down collar: The phrase gets mistakenly used to refer to button-fronted shirts of any kind, but a true “button-down” has small buttons that attach the collar points to the shirtfront. The style has working-class origins, and is considered less dressy than other collars — you shouldn’t usually be wearing button-down collars with business suits, though you’ll certainly see men doing it.

Tab collars: This collar employs a small tab extending from the middle of each point, which is fixed together – usually with a hook-and-loop closure – behind the tie. This forces the tie forward and up, creating the “standing” look of more elaborate knots. This collar should never be worn without a tie, and can be used to hide a abnormally long neck (Google image search Tom Wolfe).

Pin Collars: This collar has small holes in each point, allowing the insertion of a decorative pin or bar behind the tie knot which thrusts the tie knot forward and up while adding extra decoration to the collar itself.

Like in the tab collar, this forces the tie forward and up, creating the “standing” look of more elaborate knots. This collar should always be worn with a tie; the empty holes and flapping tabs present an untidy appearance.  Only wear this collar if you have the confidence to wield the attention it will draw.

You may occasionally run into other, odder collar styles, such as the club collar (rounded lobes instead of points), or military-style collars that don’t turn down at the neck, but these are largely not worn as part of business dress.

You might see a club collar on a very old-fashioned banker from time to time, but that’s about it. In general, dress shirts will have either a point or a spread collar. The wider your face, the more natural a wide collar spread will look under it — broad-faced men will look best in wider spread collars, while narrow-faced men do best in a closely-spaced point collar.



Cuff Styles

Dress shirts are meant to be closed at the cuff. The vast majority have buttons sewn onto the cuff for that purpose; a few styles have only holes, and are fastened with separate cufflinks instead. Cuffs can be either “single” or “double” style:

Single cuffs are much more common — a simple horizontal band of cloth at the end of the sleeve fastened with a button.Very occasionally, the button is replaced with a cufflink, but you’ll rarely see that style outside of formal shirts meant to be worn with a dinner jacket.

Double cuffs have a long band of cloth around the wrist meant to be folded back over on itself. They almost always fastened with cufflinks, called a French cuff.

Single cuffs are also sometimes called “barrel cuffs,” which is not strictly accurate — “barrel cuffs” refers to the way the two sides of the cuff overlap, with the ends facing in opposite direction and the sides laid one on top of the other.

French or double cuffs can also be fastened barrel-style, though “kissing” (with the ends pointed in the same direction, and the undersides of both edges pressed against one another) is more common. You can wear either style interchangeably.

There’s a bit of a sense nowadays that French cuffs are more “formal,” since cufflinks are seen with tuxedos so often, but a dress shirt with French cuffs can be worn all on its own, without a necktie or even a jacket, if desired. They’re a bit more noticeable, and offer a way to add jewelry to the outfit, that’s all.



A Guide To Patterns

Click on the image for a larger view of the infographic

Color and Pattern

The most formal business shirts (and formalwear shirts, for that matter) are plain white, but in most circumstances a bit of color and pattern is fine.

The brighter the color and the more vivid the pattern, the less dressy the shirt is, which is why you mostly see either a bolder pattern done in fine lines on white, or a brighter color with minimal patterning, not both at once.

White and light blue are far and away the dominant colors for men’s dress shirts. Pink also has a strong following, and various other pastels make their appearances too. Bolder colors — bright primaries, for example, that haven’t been shaded down with white or black — are usually left to casual shirts.



Casual Style A Man's Guide to StyleCasual Shirts

All the information above details dress shirts acceptable for business wear.

Most of us, however, need a wardrobe for casual life as well, and we’d like it to be a little different from our work wardrobe.

Fortunately, there’s a wide range of casual shirt options for guys, and you can mix or match from dozens of styles:

  • Dress shirts: Wear them untucked, or just tucked into jeans without a necktie and with the sleeves rolled up. Instant casual.
  • Work shirts: The slightly rugged cousin of a dress shirt, these have the same basic button-front, turndown-collar style, but are made of heavier material. They work great in basic blue oxford or in plaid, or anything in between.
  • Polo shirts: A valuable core to any man’s summer wardrobe.
  • Sweaters: Everything from a simple knit to a thick cardigan makes a good alternative to a jacket for “something to wear over a dress shirt.” For the daring, sweater-vests can be added as well.
  • Long-sleeve T-shirts: A good collarless option for wearing under casual jackets. Thin turtlenecks or knit cotton sweaters fill the same niche well.
  • Henley shirt: Either long-sleeved or short-sleeved; basically a T-shirt with a small buttoning “fly” in the middle of the ring collar. Unique and casual.
  • Guayabera: A classic South and Central American style with large patch pockets and vertical stitching or pleats. Great for the summer wardrobe.
  • Breton tops: The iconic “French” shirt with three-quarter length sleeves and alternating dark and light horizontal striping. For making a bold statement.
  • T-shirts: A plain, dark T-shirt can go under a jacket with the right jeans and the right shoes. If it’s close-fitted, it can even be worn on its own from time to time.

You’ve got a lot of options, and none of them are automatically “better” than others — try to be heavier on collared shirts (dress shirts, work shirts, etc.) than on options without the turndown collar, but a good mixture is not a bad thing to have in your wardrobe.


Is price the only way to determine a dress shirt’s quality? Click here to watch the video.





Lesson 7: Understanding Men’s Trousers





Style for your lower half. What’s in a name? Quite a bit, when you’re talking about “pants,” which in America means long trousers but in the United Kingdom means your underwear.

Many cheap transatlantic gags have been made from that particular translation error. But whichever word you’re using for it, men’s trousers don’t get nearly the attention that suits, jackets, and shirts do. Part of that’s because there genuinely are less options out there, but the options there are deserve some careful thought:


Suit Trousers GrayDress Trousers: Wool Slacks

“Slacks,” technically, can refer to any pair of trousers made from fine cloth. It’s a descriptive name; it implies that the fabric is light and finely-woven enough to hang “slack” rather than being pulled taut by its own weight.

Most high-quality dress slacks are wool, though cotton and linen versions exist. These, and suit trousers (which are almost all slacks with matching jackets), make up the dressiest end of men’s non-formalwear trouser options.

The most classic slacks are the iconic “gray flannel trousers,” which for many years were considered a business-casual staple; these days they’re actually relatively hard to find. Many places have replaced the softly-fuzzed flannel with smooth worsted wool.

In either case, however, the plain medium gray trousers are valuable for their comfort and their ability to go with almost any outfit. Other popular color and pattern options for dress slacks include:

  • charcoal gray
  • brown
  • navy blue
  • houndstooth (a decorative weave with a checkered appearance)
  • herringbone (a weave with visible V-shaped chevrons in the fabric)
  • Glen check (also called Prince of Wales)

Trouser patterns tend to be reserved, since most men look better when the upper half of their body is drawing more attention than the lower, but a bit of subtle texture in your slacks is a great way to distinguish them from the more casual chinos or khakis.


pantCasual Trousers: Chinos and Khakis

Both “chinos” and “khakis” are words with military origins, referencing old styles of uniform trousers. We’ve appropriated the words and turned them into general terms for sturdy cotton trousers that aren’t part of a matched suit.

These are worn when wool would be too formal, too hot, or simply too expensive — cotton chinos are a much cheaper way to flesh out the dress-casual wardrobe.

They have a little more weight and bulk, and are considered more casual, but they can still be sharp-looking when carefully pressed to a nice, sharp crease. Chinos/khakis are almost always a solid color, and the fabric is typically a tight twill weave with small, but visible, diagonal lines running through it (similar to the visible weave of blue jeans, but on a smaller scale).

Light tans and yellows are the most common color, but darker colors like brown, navy blue, and even black are also available and acceptable.


How jeans should fit infographic

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Jeans and Corduroys

Blue jeans have working-class origins, but they’re an integral part of men’s fashion nowadays. If you don’t have a pair you can “dress up” in the wardrobe, you’re doing yourself a disservice.

Telling work jeans from fashion jeans is easy: a stylish pair of jeans will be darker-colored, closer-fitted, and less rugged-looking than the bulky, squared-off, light blue work jeans.

They don’t have to be skinny jeans, and you don’t need a visible designer label; just a pair of deep indigo denim pants with a fitted waist and a bit of taper in the legs will go great with everything from T-shirts to sports jackets (or both at once, even).

To “dress up” jeans, wear them with a collared shirt, leather shoes, and maybe a blazer or sports jacket. Skip the necktie, however — jeans and a tie is always an awkward contradiction. And be cautious of jean jackets; you usually don’t want to mix denims in the same outfit, unless they’re very different colors and styles.

For an alternative to jeans that less men own, try corduroys: soft, textured trousers made from a fabric with ridged vertical lines. Corduroys have a less defined shape and are often cut a little roomy, making them very comfortable, and you can get them in everything from reserved navy blue to vibrant greens and yellows.

They should be treated as being the same formality as jeans — fine for social life and casual workplaces, but not for any traditional business or office setting.

 cuffPleats and Cuffs

A last consideration on trousers is the presence or absence of pleats and cuffs. Pleats are the thin, vertical folds on the front of a pair of trousers’ thighs. They’re designed to let the pants widen slightly when you sit or stretch, adding a bit of comfort.

Pleats come in and out of style so frequently that they’re never really “right” or “wrong.” In general, get them if you feel the need for the added comfort — wider men benefit from them in particular — and otherwise leave it up to personal taste. Cuffs are a folded-over strip of cloth at the bottom of the trouser legs.

They’re practical in origin — a cuff wears down less quickly than a plain hem, and it can always be unstitched, folded a touch shorter, and then stitched back into place to hide a fraying hem.

Because of the added visual clutter and the working-class origins, cuffs are not recommended for business dress slacks or suit trousers. You’ll see men with cuffed suit trousers, but it’s better to avoid the style if you can. Most men benefit from a clean lower leg anyway, unless you’re very tall and want a bit of distraction to shorten your visual impression.


What makes a trouser break so important to your overall outfit? Click here to watch the video.




Lesson 8: Shoes And Accessories




Once you’ve read about suits, jackets, shirts, and trousers, you’ve accounted for around 85-95% of your body’s covering on any given day. The rest is the accents, and they’re what set your outfit apart from other men’s outfits.

Pick thirty suits at random, and odds are that twenty-five of them, minimum, will be basically interchangeable. Quality makes a difference, but a gray suit is still, at the end of the day, a gray suit. And that means what you wear it with makes a lot more difference than you’d think.


Shoe infographic A Man's Guide to Style

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There’s an old saying that you can judge a man by the shine of his shoes. Don’t take it too seriously, but do take it as an indicator that people are looking at your feet from time to time. You want them to look decent.

Dress Shoes

For business wear, you want a pair of plain black balmoral oxford dress shoes. That’s a lot of words, but they’re all pretty simple ones:

  • Black — black leather, specifically, not a fake plastic substance. The better the leather, the longer your shoe will last and the less maintenance it will need, so be willing to invest a bit in quality here.
  • Balmoral — This refers to the way the “lacing system” is attached to the shoes. Balmoral construction means the piece of leather with the eyelets punched in it is all of one piece with the rest of the shoe uppers, rather than being separate pieces of leather laid on top.
  • Oxford — This gets used interchangeably with “balmoral” sometimes, but technically refers to the low-ankle height of dress shoes, wherein the opening of the shoe stops at the large bone of the ankle

One pair of these is an essential for every man’s closet. After that you can add more pairs with a little more decoration to them. Dark brown balmorals (or “bals”) can also work with suits in some more relaxed settings, as can black loafers or black brogues (shoes with decorative seams and hole-punching). But start with the plain black oxford balmorals.


Casual Leather Shoes

There are literally dozens of casual leather styles, ranging from “full brogue” wingtips to saddle shoes to rubber-soled boaters. These are your best go-to shoes for most daily purposes.

They work well in business-casual offices, at casual day jobs, and with your social outfits. At the bare minimum it’s worth getting a black or brown pair of work shoes (sturdy-soled leather shoes — think Dr. Martens), and most of us can find use for other styles as well.

If you’re looking for ideas, consider any of these styles:

  • brogues (leather dress shoes with decorative hole punching)
  • saddle shoes (leather shoes with a differently-colored band across the middle)
  • dress boots (high-ankled leather shoes)
  • wingtips (called “full brogues” if the leather is punched)
  • loafers (slip-on leather shoes)
  • boaters/topsiders (rubber-soled, low-ankled summer shoes)

See what works for you and what works for your wardrobe. You’ll be surprised how much “nicer” you look just by trading sneakers for casual leather shoes, even when nothing else in the outfit changes.


Sneakers and Canvas Shoes

For the most part, athletic shoes should be reserved for just that — athletics. Unless you’re a rap star (or at least hanging out in places where they perform), designer sneakers aren’t a very good fashion choice.

That said, canvas shoes do have a role in the wardrobe, particularly in “dressing down” otherwise-conservative outfits. Wearing a blazer and nice slacks to a night club, but don’t want to look old-fashioned? Throw on some red Converse sneakers and suddenly you’re a hipster. For a more exotic look, there’s espadrilles, hemp-soled canvas shoes of traditional Spanish construction.

These have become increasingly popular as, again, a way to look younger and more casual while wearing fine trousers or jackets. Just note that these are all canvas shoes, rather than rubber, and that they’re worn only in casual situations. Most of your shoe needs should still be met by leather.


Accessories and Jewelry

Most men wear few accessories. That’s fine, and as it should be, but don’t be afraid to add one here and there where it’s appropriate. Like your shoes, your accessories are how you personalize the somewhat generic template of menswear.



Belts for business situations are easy: they should be slim, leather, in the same color as your shoes, and buckled with a small, metal buckle. Nothing ostentatious or decorated. You can even omit the belt entirely and go with suspenders (“braces” in the U.K.) instead, if your pants are made to take them. For the rest of your more casual situations, belts can be a neutral piece or a decorative one.

Woven or stamped leather, colored cloth, and large buckles are all ways to draw a little more attention to your belt. It’s a good way to add visual interest if the rest of your outfit seems a little generic, but don’t wear a decorative belt with too many other eye-catching accents. It’ll get too “busy.”


Dress WatchWatches and Jewelry

A watch is always worth wearing. It shows that you’re prepared, and has a little bit of luxury to it as well, as long as it’s not a plastic sports watch.

Either metal or leather bands are fine, just remember that both are subject to matching rules: all the leathers in your outfit should be the same general shade, and the same is true of your metals (except for a wedding band, which gets an exception because you’re always wearing it, at least in theory).

Other jewelry can be worn so long as it is limited in both style and quantity: one small, decorative ring is fine; two on each finger is not.

A fine gold chain worn with a black T-shirt and a blazer can work as a nightclub look; drapes of thick links all over the place just makes you look like a jerk. And so on — exercise some restraint, and keep your metals matching, and there’s no reason you can’t wear rings, necklaces, earrings, cufflinks, watches, or bracelets. Just exercise that restraint.



For the most part, neckties aren’t casual wear, but there are exceptions. A colorful necktie is fine any day you want to look a little sharper and more clean-cut, for fun or for business reasons.

Bow ties work as well, and have a little bit of a quirky, novel feel that makes them slightly more of a fashion statement than a regular, straight necktie.You’ll almost never wear a necktie at night, even in fairly formal settings.

There may be the occasional late-night business meeting or legislative session that sees men stuck in their suits and ties well past sundown, but the unofficial rule of thumb has always been that, if you’re not at work and it’s after 5:00 PM, you don’t wear a necktie.


rubens-samson-and-delilah-pocket-handkerchief-fold-2_grandePocket Squares

These are an under-utilized tool that every man should take advantage of. A pocket square (a piece of fabric worn visibly in the breast pocket) is your personal touch on a jacket. Use it to complement (but never match exactly) your necktie, or opt for a plain white square in a horizontal fold for the most formal look.

If you wear a jacket, it should have a pocket square in the breast pocket. There’s really no exceptions to this one. Anything else is just cheating yourself of a fashion opportunity.


Want to upgrade your shoe collection? Click here to watch the video.





Lesson 9: Coats And Outerwear





What you wear on top of what you wear. A good suit can be ruined by a bad overcoat — most people’s first impression of you is what you’re wearing when you come in from the outside, and for a lot of the year that’s not actually the “outfit” you picked out in the morning.

Whether you’re wearing it for business purposes or casual style, you want to put a little thought into your outerwear.


Click on the image for a larger view of the infographic

Dress Overcoats

The most important rule for your dressiest coat: it has to be longer than any suit or sports jacket you wear it with.The hem of a suit jacket sticking out from beneath an overcoat is always a bad look.

Avoid it by investing in a long coat: either a wool dress coat style like a polo coat or Chesterfield, or for a more casual look a canvas trenchcoat. If you’re wearing a suit, you usually want one of the wool styles; trenchcoats are a little casual for suit-and-tie affairs.


Casual Overcoats

Most men are surprised by how many “stylish” coats there are out there. You can look quite sharp without looking like you’re going to the opera.

Casual coat styles tend to be shorter, indicating that they’re not usually worn over a suit jacket or a blazer (though many do come down to the upper thighs so that you have that option).

  • Leather jackets are tough, practical, and instantly “cool.” Bomber jackets give you a bulkier, more practical look, while moto or “double rider” style jackets are slimmer and give you a motorcycle-riding tough-guy aesthetic.
  • Jean jackets look simple, sturdy, and working-class, which is not a bad aesthetic for your off-hours. Just be careful not to wear them with jeans. One piece of denim in your outfit only!
  • Peacoats are a thigh-length style popular among young men. It’s a gender-neutral style, so you’ll see it on girls as well, but don’t be afraid to wear one — the style originated with (male) British sailors.
  • Blousons and field jackets are military or military-inspired styles that stop at the waist. You can’t wear them with sports jackets, but they go great over sweaters, T-shirts, and other casual tops.

There’s plenty of other styles out there — don’t be shy of owning more than one middle-weight coat, as well as your heavy-duty winter jacket. A variety of styles never hurt anyone.


“Working” Overcoats

Everyone needs a few purely practical pieces in the wardrobe. You can still opt for a stylish version, but be sensible when you buy your “working” coats:

  • Parkas: The heavy winter jacket needs to be exactly that — heavy. To keep it stylish, try for one with a flat canvas or cloth exterior, rather than slick, puffy plastic. A waxed cloth exterior is just as water-repellant as synthetic, and much better-looking.
  • Raincoats: A simple waterproof shell works fine, but for a little more style consider something like a Barbour jacket, the British style of waxed-cotton field gear. They have more body and are cut with a deliberate style, rather than looking like a disposable slip-on covering like most plastic ponchos.

Remember that even when you need legitimate protection from the elements, your top layer is still your first impression on the people around them. Do what you can to add a little style to your practicality, and you’ll stand out from nearly everyone in the crowd.


How do you figure out which style of leather jacket will look good on you? Click here to watch the video.





Lesson 10: Dress Standards And Dressing Well For All Events





The most important lesson: how to always look good. Is there a single rule that will always make you look good? Not really — but if there were, it would read something like “dress to stand out without breaking the rules.” That means knowing two things: what stands out, and what the rules of the situation are.

Everyday Casual: How to Dress for Yourself

Most of our lives are not spent in a situation with “rules.” When we’re out on the street we don’t have to follow any dress code but our own. So what do you wear? You wear what you want. But, you do it in a way that looks appealing to others as well. Remember:

“Casual” doesn’t mean “sloppy.”

Fitted jeans, a dark T-shirt, and a sports jacket is “casual.” Loose work jeans and a T-shirt with a band logo on it is “sloppy.” The two are not the same thing. A good day-to-day style means upgrading a few minor things so that your outfit looks deliberate.

Wear nice, decorative leather shoes. Throw on a jacket and a pocket square. If you don’t have anything else going on in the outfit, wear a colorful canvas belt with an artsy buckle. That sort of thing — have a few gestures in there that say “I thought about this outfit.”

If you look around a busy street, you’ll notice that most men don’t have that look. That’s who you’re trying to stand out from.


Office Casual: Dressing for the Job

Most of us do not work in suit-and-tie industries. Our work wardrobe is centered around slacks and dress shirts, not suits.

To stand out in that sort of situation, picture the “corporate drone” look — khaki pants, blue or white button-down shirt; necktie — and figure out ways to depart from that.

Throw a casual jacket on even if they’re not required in the office. Wear a bowtie. Invest in some stylish leather shoes. Use sweaters. Add minor pieces of jewelry. Heck, just get a slightly stylish haircut and you’re already ahead of the game.

Your competition is usually making it easy on you in an office setting, so don’t overdo it — there’s no reason to show up for work in a three-piece suit just because you’re trying to dress a little sharper lately.

Make small but deliberate improvements and it’ll get you the results you want.


Click on the image for a larger view of the infographic

Business Formality: Dressing to Impress

We say “business dress” when we’re talking about suits and ties, but these may have occasions in your life outside of business — weddings, funerals, award ceremonies, etc. In any event, business dress usually means a dark suit, a white shirt, black shoes, and a necktie.

For your most formal situations, don’t deviate from that at all. Wear the best-quality pieces you can afford, but stick to the formula. In a slightly more relaxed (but still suit-and-tie) setting like a wedding, be willing to play around a tiny bit — wear a lightly-patterned, white-based shirt instead of plain white, for example, or substitute black brogue shoes for plain black oxfords.

Even just a colored pocket square instead of a plain white one makes a bold statement against a business suit’s backdrop.


Conclusion: Dressing Well Means Dressing Like You Thought About It

That one sentence should be your guideline for all situations: dress like you thought about it. If your outfit appears deliberate, you look sharper than the guy who just threw on something that met standards.

Small, simple touches do all the work for you — better shoes, colored accents; a good fit. Personal choices are the lever with which you move your stylish world. Don’t be afraid to make a few.

Curious about “optional” dress code? Watch this video.


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