How Clothes Should Fit on a Man (+ 5 Ways to Get it Wrong)

Guy wearing oversized shirt
This guy is making a critical mistake

You probably make this one crucial style mistake.

Most men do.

Even if you get everything else right, you ruin your look by getting this one thing wrong. And you don’t even realize you’re getting it wrong.

Because you don’t know how clothes should fit on a man.

You keep wondering why clothes don’t look as good on you as they do on others, and it’s likely because of this one basic error.

Fixing this mistake is the most important change to your style. Leave it unfixed, and all your efforts to dress well will be fruitless.

So even if you think you’ve got this down, you might want to read on to make sure.

The mistake I’m talking about is wearing clothes that don’t fit.

What Makes Fit So Important

If you read my post with 13 fashion tips for beginners, you probably noticed that several of them mentioned fit.

This happened because the fit of your clothes for a large part determines whether your outfit looks good on you or not.

bad fit vs good fit suit
Spot the difference?

You will never be a better dresser if you wear clothes that don’t fit correctly.

If something doesn’t fit, then it never looks good, no matter how hot you think the item looks on the rack.

Well-fitting clothes will complement your body, whereas ill-fitting ones will draw attention to your problem areas.

When you wear clothes that fit well, you’ll not only look, but also feel better.Your posture appears better, which affects the way you (and other people) perceive yourself. You’ll feel a lot more confident.

This is why fit is such an important aspect of style.

So why do guys keep making this mistake?

5 Types of Guys Who Wear Ill-Fitting Clothes

Guys wear ill-fitting clothes for a number of reasons, but there are 5 main types of guys that show up the most:

  • The Body Hider is unsatisfied with the body he has and tries to hide it from the world. They wear clothes that are too large to try and cover up their problem areas, but in doing so, they’re only drawing attention to them. Skinny guys that do this will only be perceived as unable to fill out their own clothes. Large men will only add bulk to their frame.
  • The Body Smoother thinks he can smooth out his belly bulges by wearing tight clothes. He doesn’t realize this will only make them more prominent.
  • The Oblivious doesn’t realize he’s doing anything wrong at all. He thinks everything is okay, unless you can’t physically put an item on without tipping it. He’s simply clueless on how clothes should fit properly.
  • The Indifferent doesn’t think fit matters that much. If an item looks cool on a mannequin, it will also look cool on him. Who cares that it’s a bit oversized?
  • The Show-Off is the opposite of the first 2 types, and is actually so proud of his muscles that he wants to show them off. He wears a shirt that’s so tight it nearly cuts off his circulation. The only thing he shows off though is his douchiness.

Usually a guy is a mix of 2 of these types. I was an oblivious-indifferent combination.

Which type do you think you are? Be sure to let me know in the comments.

How Clothes Should Fit on a Man

Clothes should fit the body you have now; not the one you aspire to have. Sometimes people will buy clothes in smaller sizes, because they intend to lose weight. This is a faulty approach.

You should never base your wardrobe on a future projection of yourself.

Properly fitting clothes feel comfortable. They drape over your body without stretching or billowing. They accentuate the lines of you frame.

Here’s a quick checklist you can use to evaluate different items.

shoulder seams
Shoulder seams should be on the edge of your shoulders


  • Shoulder seams should rest on the edge of your shoulders; not on top of them and not over them.
  • T-shirts shouldn’t pass your zipper.
  • When you raise your arms sideways, no more than an inch of your belly is exposed.

Different brands cut their T-shirts in slightly different ways, so you have to find the store that has the closest fit for you. If you want to have an idea of what size to go for, try this T-shirt size calculator.


  • Check the shoulder seams the same way as with T-shirts.
  • The cuffs of your shirt should end at the dimple of your wrist.
  • There’s no stretching of fabric around the chest or the buttons.
  • When you tuck the shirt in, there is no excessive billowing around the waist.
  • You can fit two fingers between the collar and your neck; no more and no less.

Click here for a more detailed shirt-fit checklist.

pants fit
Always try pants on without a belt. You should be able to keep them up on your own.

Pants / Jeans

Here’s how your pants and jeans should fit:

  • Your pants should feel comfortable around the waist. They should not fall down when wearing them without a belt, but they shouldn’t be pinching your waist either.
  • The front of your pants leg should have a slight break, where it meets your shoes.
  • The back of your pant leg should just reach the top of your shoe’s sole.
  • The fabric at the end of the legs shouldn’t puddle.


  • Check the shoulders and chest. The jacket needs to fit in these places, as they’re the hardest  to alter.
  • Your lapels should lie flat against the front panels and the buttons should hang close to your stomach.
  • The shoulder seams should rest at the corner of your shoulder, and the sleeves shouldn’t have indents below the seam.
  • Cuffs of your shirt should protrude about a quarter to half an inch from the jacket’s sleeves, when you’re standing with arms hanging by your side.
  • When your top button is closed, the jacket should show no X-shaped stretching.
  • The jacket should just about cover your butt.

Action Step 1: Evaluate Your Current Wardrobe

What I want you to do next is take all the clothes you currently have in your wardrobe and use the above checklist to evaluate each piece.

Try everything on in front of a full body mirror, and go over each checkpoint to see if it meets the criteria. Also be sure to check whether the clothes follow your frame or have too much fabric.

There’s a good chance many of your clothes will have the wrong fit. This doesn’t mean the end of the world. A lot of them may still be salvageable. If an item is worth the additional investment, consider getting it tailored.

And what of your truly poor fitting clothes?

donations box
Charities will be more than happy to accept your old clothes

Most fashion sites will tell you to chuck them. Donate them to charity, give them to a friend, or just throw them in the trash.

Since I was a bit of a clothes hoarder though, I didn’t follow that advice. I kept all my clothes around, while I worked on my style. I just kept them somewhere separate.

Then, after working on my style for a while, I took them out and tried them on in front of a mirror again. It was a great way to really get a visual on my progress.

After that I chucked them, and now I regularly prune my wardrobe and chuck whatever I no longer wear.

And you should prune your wardrobe periodically. But for now, hang on to a few items and look back on them after you’ve improved your style a bit. You’ll get a kick out of it.

Action Step 2: Take This Checklist Shopping

What I also want you to do is bookmark this page in your phone, or print out a copy. That way you’ll never forget to check something when you go shopping for new clothes.

It’s a lot to remember, so it’s good to have a reminder with you until you’ve internalized all the checkpoints.

Even after I figured out how clothes should fit on my body, I sometimes forgot to check things. I still came home with T-shirts where the seams went over my shoulders, or jeans that I couldn’t keep up without the help of a belt.

So keep this checklist with you!

Take Action and Improve!

If you’re someone that’s been wearing the wrong fit of clothes, then the above action steps will help you immensely. The effect this basic fix can have on your look will astound you.

When I first evaluated my wardrobe with a similar checklist, I discovered more than half my clothes didn’t fit right.

How many items in your wardrobe did you discover were ill-fitting?

Did You Find That Useful? Then Check This Out…

I wrote a men’s style guide that simplifies the art of dressing well, focuses on what matters, and takes you through it one step at a time. Enter your e-mail below and you’ll receive three free chapters, which will show you:

  • How to build an easy-to-match wardrobe
  • How to make shirts look awesome on you
  • How to create flattering clothing combinations

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