How to Dress Like a Man

how to dress like a man

Who are we to argue with the words of the great American philosopher Ralph Waldo Emerson when it comes to dressing well?

“Being perfectly well-dressed,” observed Emerson, “gives one a tranquility that no religion can bestow.”

Strong words, indeed. And certainly words to keep in mind as you decide that becoming a grown man means dressing like one.

What would you rather have: the peace and contentment that comes with knowing you’ve dressed your best or the turbulent ways of someone who embarks on each day in a state of sartorial sloppiness?

You know what you’d choose. But here comes the hard part: perhaps you don’t know where to begin or have the faintest idea how. What follows are some tips, fundamentals, and suggestions that can help you look your best and, as Emerson states, feel your best.

1. First Things First

To start at the beginning, at the most fundamental level, big things are made possible by one small word: F-I-T.

Men’s fashion experts nearly all start with the fit; if the clothes don’t fit, it doesn’t matter how good they look. A kid in an ill-fitting suit looks cute. A grown man in an ill-fitting suit … well, enough said.

Some basic rules about fit:

  1. Fit always matters, except when the clothes are all wrong for you. Ridiculous clothes that fit well are still ridiculous.
  2. Generally speaking, it’s a good fit if the clothing sits close to your skin without pinching or constricting.
  3. Learn your measurements. Many men buy suits that are too big, sometimes two sizes too big. Also, learn how to layer your clothes the right way.
  4. While your shirt should rest flat against your skin, your pants should provide a little more room, but don’t go overboard and turn a “comfortable” fit into “saggy.”
  5. Bring a pair of dress shoes along with you if you’re trying on pants. Know that the fit is off if your pants aren’t touching your shoe or they’re so long that there’s a bunch of cloth piled up on it.

There are so many other things to be said about fit. Just remember, how your clothes fit on your body affects the way others look at them more than anything else.

2. Keep it Simple

It might seem like a daunting task, especially if you go in without a lot of knowledge, but dressing right isn’t rocket science. And simplicity is your friend.

Being a man doesn’t demand a vast wardrobe of extravagant clothes. The key is to start thinking outfits, instead of individual pieces of clothing. Think versatility.

Here are some how-to-dress-like-a-man wardrobe essentials that will help you make the most (outfits) with what you have.

Charcoal Suit

charcoal suitWhat’s not to like? A two-button charcoal suit works at a dinner party, a job interview, a wedding (guest, of course), and even a funeral.

As already mentioned – and will likely be mentioned again – fit is everything.

If you need to take it to a tailor after buying it off the rack, so be it.

V-Neck Sweater

v-neck sweaterA wool v-neck sweater, that is.

When the weather turns cool, put on that v-neck over your dress shirt to add some variety to your wardrobe.

Grey V-Neck T-Shirt

grey v-neck t-shirtMust have it.


Because it works it so many ways; as an undershirt, under a dress shirt, or by itself with jeans, pants, or shorts.

Keep a couple of these to have in the rotation.

Dark Jeans

dark jeansA good pair of jeans works with just about anything.

Go with straight leg, slim fit, and unwashed.

Avoid crazy stitching and additional design, because the point here is to dress like a man.


black oxford shoesShoes may seem like an afterthought, but experts say they can make or break an outfit.

Seriously guys, shoes are a big part of the big-boy game, and if you’re really committed to dressing like one, then don’t skimp with cheap shoes.

There are two styles you should shop for: a black oxford and a brown lace-up.

The black oxford is the most formal pair you’ll own and is good for any occasion, including your own wedding.

The brown lace-up is an everyday shoe and less formal, but it is extremely versatile and can be paired with any color except black.

For casual wear, a pair of low-profile canvas sneakers is a safe bet. Not athletic shoes, mind you.

In case you are standing all day, it would also be good to have a pair of shoes for that. Wear those when you work out, but that’s it. Period.

However, if your job involves standing through most of the day don’t skimp on comfort.


white oxford cloth button down shirtAdd a white oxford cloth button-down shirt to your closet, as well as a blue or purple gingham shirt.

The white button-down works in the office or at a casual party, while the gingham gives you the smart casual look.


short sleeve polo shirtA plain-colored crew neck t-shirt will always be a go-to option, but a short-sleeve polo when the weather warms is the next rung up on the sophistication ladder, because it has a collar.

Navy Blazer

navy blazerGoes with just about anything. Instantly dresses up your outfit.


That’s why the navy blazer makes the cut.

3. Eliminate The Same-Old

Nobody wants to be the man who wears the same outfit – or two – all the time. Yawn.

You need variety, versatility, and simplicity, which might seem like a hard thing to accomplish but really isn’t if you keep an open mind. So, open your mind to new types of clothing and try new things you’ve never worn before.

Sometimes, that item you always thought ‘wasn’t you’ can look amazingly good.

The days of your mom dragging you off to try on school clothes are a speck in your rearview mirror. Nobody’s forcing you now, but take your time. Trying on everything will give you a greater sense of style.

4. Don’t Go Fashion Crazy

Fashions come and go. They’re too hard to keep up with. So, don’t worry about them.

Your goal is to dress like a man, and dressing like a man means having the right wardrobe staples that will always be in style. Same thing goes for things like your wallet, for example.

5. Fabric Is Your Friend

fabric is your friendFabric is right up there with fit, and knowing a few basics can make a huge difference:

100% Construction

If it’s all wool or all cotton, it should be just that. A small percentage of synthetics is livable, but when you go lower than 95% base material, it’s most likely cheap fabric.

Right Weight

Feel the weight of the item in your hand. Yes, it’s an inexact science, but stay away from anything that seems flimsy. It should have enough heft to drape smoothly when you wear it.

Check the Weave

Be on the lookout for imperfections on the surface of the cloth. If you see holes or snags, put it back. If the spacing is uneven, or some bumps and knobs are bigger than others, you also have a problem.

6. Take Care Of Your Clothes

Again, you’re a grown man. Take care of your stuff. Hang your suits on good hangars. Invest in a shoe tree. Maintain your investment and wash with care. You’ll look better in the process.

7. Grooming

We’re talking about dressing like a man, but grooming is certainly an integral part of the overall look.

Thinking about growing a beard? It will only add to your manliness points and bring with it a variety of benefits, including more attention from the ladies (it’s a scientific fact).

Don’t, however, shave your legs or arms or pluck your eyebrows. After all, we’re trying to be men here. If you like to drink on the go, try using liquor flasks.

About The Author

Domen Hrovatin
Domen Hrovatin

Domen—a self-confessed facial hair addict—is a grooming professional, style enthusiast, and someone with deep personal experience and knowledge about male pattern baldness. His work was mentioned in countless notable men's grooming and style publications, including Beardbrand and AskMen.

  • Such a good post there, very good advice, remember also when you wear a dress shirt to also wear a tie to match. Grooming is also very important, yes I do agree that no man should shave his legs or arms, however if you are a club swimmer or cyclist you might just get away with that, but other wise ‘keep it natural’. I have just grown a beard for the second time, I tried on a dress suit with a tie and yes my beard makes me look very manly as well.

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