How To Dress Like a Man

Guys, here is your one-article guide to dressing, based on many years in the rag business and a lifetime of observing the sheer ubiquity of error.

There are two general types of men’s clothing.

First, there are clothes for public consumption: clothing in which to present yourself to others and thereby convey an elevated message about yourself. These are types of clothes you wear to work, to the store, out on the town, at a wedding, at church, at parties, or wherever people are going to see you. The primary objective here is that you look presentable, that you are civilized, a gentleman and not a beast.

The other type of clothing is that which serves a pure functional purpose: that is, that which you wear for yard work, fixing your car, an evening at home, a Saturday washing the house or cleaning, or just knocking around the park with kids. Everyone knows what type of clothes these are. They can all be bought at Wal-Mart or thrift stores, and they are made of cotton.

The great dressing error of our time is to confuse the two. Or more precisely: people think that it is perfectly okay to present yourself to others in clothes which serve a purely functional purpose. They say this is fine because it is comfortable — as if the only thing that matters in life is comfort. Well, it is also comfortable not to shave and not to bathe, and we have a word for people like that: slobs. If you don’t want to be a slob, you have to live with a bit of discomfort.

If men could absorb that simple lesson, the world would be a much more beautiful place in which to live. Elevated dressing causes people to behave better. Crime might fall. Manners would begin to come back. People might clean up their language. They might listen to better music and read better books. Something resembling civilization might return.

Now the next step: how do you look presentable? For a man, it is a snap. Your full wardrobe need not take up more than 12 to 18 inches of closet space. You need:

  • one or two suits in blue or grey
  • a blue or black jacket or sports coat
  • a jacket for summer (khaki or blue cotton or, if you want to be really fancy, seersucker)
  • a tweed jacket for winter
  • year-round grey wool trousers (light or dark or both)
  • a few pairs of khakis
  • 3 white and 3 blue shirts
  • a selection of ties

That’s all. That will get you through a lifetime, replacing them with something similar when these wear out. Mix as necessary. If you have chosen well, just about any jacket will go with your trousers. Just about any shirt will go with any jacket. Ties should be chosen with an eye to color, making sure that the tie stands out and does blend in with either jacket or shirt or trousers. Men’s clothes should not “match”; they should go together, which is something else entirely.

But, you say, I’ll look the same all the time! Right. This conveys an impression that you are a wise and stable person, not prone to flights of fancy and fits of fashion. There is a practical aspect here. You don’t really want to wear clothes that cause people to comment: hey, that is a really nice forest-green, window-pane, double-breasted, peak-lapel, side-vent hunting jacket with leather patches! The next time you wear it, the comment will be: oh, you wore that last week! No, you don’t really want people to zero in on your clothes as if they have an existence apart from you and your character. Clothes should not make the man; they should be the man.

As for adjustments, there are many things you can do to vary your wardrobe. The main trick here is obvious: you can switch ties around (only two knots are permissible: the four-in-hand or the half Windsor.) You can wear suspenders. You can have button-down shirts or plain collars. You can stick a linen handkerchief in your pocket. You can add a hat. All these things can make a world of difference, and make you look just different enough to make it appear that you have a huge wardrobe but not so different day to day that you come across as a loon.

Is this an expensive undertaking? Not in any way. Unless you have some size issue at work, most of this can be purchased at a thrift store. The other day I bought a pair of grey wool trousers and olive wool trousers at $3 a piece. The same items were available at a local men’s shop for $90 and up. Down with retail! Sports coats are the same: unless you have some size issue to deal with, most are available at thrift stores. Shirts? Same. A buck a piece. Another option is the wonderful shirts from Lands End. Why spend $65 for a Gitman when you can spend $25 at Lands End?

Note that wearing a sports coat is not dressing up. A sports coat and trousers are casual wear. It is mostly what you should be wearing to light parties, most jobs, to the store. It is perfectly presentable for public consumption. But do not be deceived into thinking that you are “dressing up” when you wear them. A sports coat and trousers are the official uniform of a man who is just going about the business of life. When someone says, come casual!, this is what you wear.

Jackets can have two, three, or four buttons. They can have side vents, center vents, or no vents at all. Avoid double breasted until you have everything else. Americans do not wear hard-shoulders! Nor do Americans wear those crazy drop-lapel sexy-style models that Bill Clinton wore. Do not buy these under any circumstances. They are ridiculous. Finally, always prefer natural fibers over synthetics.

Suits are trickier. You can get them at thrift stores, but they are harder to come by. You can also see Ebay, which has an amazing selection of suits that you can buy for $20 and up. If this doesn’t work, you have to go retail, and here you have to spend $450 and up for a decent suit. The worst thing to do is go to a department store and buy a $200 suit from the likes of JC Penny. These look horrible and they will fall apart. If you can’t go thrift or Ebay, prepare to spend. It is worth it. A special note for older men: wear suits most or all of the time, and always ties. Ultimately, it is the only thing an older man looks good in.

If you are wearing a suit, you are dressed up but you are not formal. For formal wear, you need a dinner jacket and black tie. That is another subject entirely. These days, most people don’t need formal clothing. If you do need it once or twice in a year, it is worth it to buy the whole package. Don’t spend a lot of money! In formal occasions, guys all look the same anyway, and you don’t wear it enough to wear it out. You can get away with spending $150 in some discount formal shop. But I digress.

On shoes, there are only two brands that qualify as quality shoes: Allen Edmonds and Alden. All others are junk. Good shoes are expensive. Prepare to pay. The best possible shoe is the shell cordovan from Alden, starting at $440 and up. So it is. They last a lifetime. If you don’t have the money, go to the military supply store and pay $10 for some used military oxfords. They look great! Ultimately, you need: a black shoe, a burgundy shoe, and a casual shoe (this, again, leaves aside shoes that go with functional wear). That’s all. As for loafers, they are aptly named. The normative men’s shoe should have laces.

This takes us to the issue of fit. Most people buy their shoes too small. Get a half size bigger than you think. Shoes should not hurt your feet. Don’t believe your shoe will stretch. It should be right when you wear it out of the store.

Fitting a shirt is not hard. Measure your neck with a tape measure. A shirt should not be too loose around the neck (you should not be able to stick your whole hand in your collar!) nor should it be too tight (when you turn your head, your shirt should not turn with it). The sleeve length should be such that the cuff hits that bone at the top of your hand some 4 inches above your thumb.

Do I really need to say it? No short-sleeve “dress shirts” in public, ever! Also, do I really need to say this? Shirts are not supposed to be worn against the skin. Wear a T-shirt, please.

Jackets: most men wear them too tight! Resist the temptation to get them taken in. They should be loose and comfortable. Jacket sleeve length: men tend to wear them too long! One-quarter to one-half inch of your shirt cuff should show below the jacket. You should measure this standing in place.

It doesn’t matter what your life activities are: fit is fit! I once had a drummer tell me that he needs his jacket sleeves long in order for them to look right as he plays his cymbals. Well, if so, I should make mine long to change a lightbulb! This is nonsense. There is only one way a jacket fits: properly.

Trousers: they are not supposed to fit like jeans! They are supposed to be loose and even bellowy by blue-jean standards. Do not have the seat taken in. Do not have the back leg taken in. Just wear them as they come. The length of leg should hit the top of your shoe. It should not break too much. Cuffs should be 1.5 inches, no less. Older men can get away with larger cuffs but not younger men.

Socks: nothing fancy, please! They should be blue, black, grey, or tan. Anything else, like argyles or other patterns, is too fussy for a gentleman. They conjure up an image of a guy rifling through a sock drawer try to find just the right sock for the occasion. This is an awful image. Socks should appear to be put on without any effort or thought. But: never wear a sock that is a lighter color than your jacket. No time to explain why. Just trust me on this point.

Finally, never underestimate the power of the iron. The iron is the ultimate tool for dressing well. It puts the crease in your trousers and takes the wrinkles out of your jackets. It flattens the placket on your shirt and puts a point in the cuffs of your pants. Your iron should come out frequently, almost daily in fact. If you are not ironing, you are not dressing well.

Yes, there is much more to say, but this article contains just about all you will ever need to know to look better than most every man in the world. Follow my advice and do your part to save civilization.

Jeffrey Tucker [send him mail] is editorial vice president of

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