How Clothes Should Fit a Man: Fashion Is Your Wingman

Let’s be honest...most of us aren't GQ models. What we are though, are men.  And as men, it's about time we learned the basics of personal style.

 I know, you learned that when you were three years old, right? That might be true, but now it’s time to grow up and start dressing with real purpose.

The rules have changed again and now we're judged on our personal style more than ever before.

Let's get one thing out of the way right now: the simplest and most basic "hack" for personal style is considering how your clothes fit you. Contrary to popular belief, finding your perfect fit doesn't have to be difficult.  Learning how clothes should fit a man is one of the easiest ways to drastically improve your personal style.

Once you come into your own sense of style, you’ll honestly feel better about yourself. No matter what the occasion, a look well put together, with the right fit, will always put all eyes on you.

Just take a look at Daniel Craig in 2004 vs 2014.  Same guy, different style.  Sure, the clothes he's wearing in the picture on the right are more expensive, but they also fit him like a boss.  He looks like an accountant in the first picture, and James Bond in the second.  Proper fit is the reason for this shift.

How can you Daniel Craig-ify your wardrobe?  Like anything, there are a few simple rules you need to follow.  Follow them, and your confidence will skyrocket.  All of a sudden that cute redhead isn’t looking past you, she’s looking right at you.

Simply dressing well won't make all women instantly flock to you (nothing will), but you'll at least catch their eye if you're put together well.

Before we begin, keep these points in mind.

Your size isn’t an issue. Whether you are thin, square, rectangular or sphere-shaped, clothing exists that will fit you. Designers are aware that not everyone is a Calvin Klein model, so rest assured that you will find an outfit that will compliment you and make you look the best you can.

Your real size looks best on you, whether you’re an XS or an XXL. Yes, always be the healthiest you can be, but don’t let your size cramp your style.

The tips below will detail how to wear a few pieces that should already be in your closet. Take into consideration your size and how you want to feel in your clothes. Rules are sometimes meant to be broken, so feel free to tailor these recommendations to your personal circumstances.

Dress Shirts

Have someone measure your neck and arm length and never forget your shirt size. They will measure your neck and arm length and will read as such, 16 ½ 34/35. The first number will correspond to your neck size and the second will be your arm length.

As regards to fit, the shirt should be neither too tight nor too loose. You should feel comfortable around your neck and shoulder area, with the ability to move your arms with ease.

Relaxed fit? Slim fit? Modern fit? Your shirts will say many things on them, all referencing the cut of the actual shirt. 

  • Slim, modern, and skinny fits will be more tailored in on the sides creating a slimmer look.
  • Relaxed fits are very similar, just not so tailored in at the waist. 

If you are not a slim person, a relaxed fit will best compliment you or even a modern fit. If you are a very slim person stick with skinny or slim fit shirts, there is nothing more wrong than seeing a huge shirt on a skinny guy. Try multiple cuts of shirt to see which style will flatter you the best.

Again purchase your real size don’t just grab anything. If you need to ask why, just look at the picture above - going even a size up can have disastrous style consequences.

Ask for help if necessary. The proper size will look perfect if you are wearing the shirt under a jacket, blazer or suit. The cuff of the shirt will come out slightly which is how it should be worn.

Blazers and Suit Jackets

Get measured properly. The number of your suit jacket will be a different from a shirt number and you should never forget this number.

You will see the number read as 40S 40R 40L.  The S/R/L corresponds to the size in the shoulders, which will trickle down to arm and pant size in a suit. S will be for shorter guys; shorter arms and legs. R will be for average height men. L will be for tall guys.

If you see a section of suit separates, then that is the section you should choose to shop in. You will find a jacket specifically to fit you then you will find the matching pants that best fit your real size.

Buying complete suits fine if that’s all that is available, but you may need to tailor the suit slightly.

Your suit or blazer jacket should fit comfortably buttoned and not lift up on the back collar or look constrained. You should be able to move your arms freely.

Some people feel you should be able to move yours arms anywhere you want, but that’s something you do when the suit is unbuttoned. Buttoned up, your suit should flatter you and allow comfortable movement. Sitting down or gesturing extremely big will be done with the suit opened.

The suit above is wrong for a lot of reasons.  The pants are too baggy, the jacket is too big for him.  All in all, his main problem is FIT, like most men.  A tailor could clean this up for him, but the better choice would be to buy a better-fitting suit from the get-go.

Find a good tailor and treat him better than you treat yourself. A good tailor is hard to find, so when you do, don’t let him go! He’ll be able to adjust the suit or jacket to the perfect fit for you.

An opinion of many is what button to button on the suit. Some just button the top button and not the others, but at this point everyone is just happy to see you in a suit, so don’t sweat the minor details.


Jacket rules somewhat apply in the same way to coats. Make sure you're wearing the right size. Not smaller or bigger.  Keep in mind what you’ll wear underneath the coat, which can affect the way you will look in the coat.  Try different styles like traditional, double breasted or pea coat and see which one will flatter you best.

​And whatever you do, don't wear something like this:

It's too long, the sleeves are eating his arms, the color clashes with the rest of his outfit, and it doesn't even come close to fitting him.  Avoid!


  • Please wear your size. Don’t wear a size bigger or smaller. Remember you will always look best in your real size.
  • Sizing of the pants will appear as this; 32/34. The first number referring to your hips or waist and the second the length in leg.

Pants should not be baggy or too wide in the leg. They should fit nicely and you should be able to walk around comfortably.

Relaxed fit? Skinny fit? Your pants will say different things on them. A skinny fit or slim fit will be cut slimmer on the legs. A relaxed fit will be more lose. A relaxed fit is where you should stop anything bigger will be baggy and don’t even look in the direction of a boot cut fit. Just don’t do it.

On dress pants or chinos you have options to cuff or not to cuff and that’s a personal choice and do whatever feels right.

Pleats or no pleats? Pleats on a suit pant are fine but peats shouldn’t make an appearance anywhere else in your pant wardrobe.

The man in this picture is breaking all of the rules.  Like we mentioned, it's OK to break a few, but not every single one.  The pants he's wearing are very baggy and a bit too long, making them bunch up at the bottom and make him appear shorter than he already is.  If he went with a slightly slimmer look that fit him better, this outfit would be much stronger.


At some point in your suit purchase you will buy a tie. Watch YouTube videos if necessary and learn to tie one. It will be something that you must do on your own, there’s no getting around it.

Skinny ties aren’t for everyone, but bulky huge ties will date your look. Opt for a slim tie which will bring you up to speed with what’s happening in the real world.  Whatever you do, don't rock a tie like this:

It's weirdly shaped, not quite thin enough to be a skinny tie and not quick thick enough to be a traditional tie, and the color clashes too much with the rest of his outfit.


  • Don’t overthink a shoe purchase.
  • You need a dress shoe, a dress boot, a pair of sneakers and a casual shoe in your wardrobe.
  • Again wear your right size. Please.

Pick colors that will go smoothly with your wardrobe. A black and brown shoe will typically mesh well with anyone’s wardrobe choice.

Shoes should fit comfortably on the feet with ease when walking.

Wear the right shoes for the right occasion. Workout or running shoes be worn when you are involved in those activities only. A dress shoe for a dressier occasion or evening. Tennis shoes or loafer type shoes for back yard events or small non formal parties or throughout your day.

Go Forth In Style

It's a lot of information to take in, but the truth is it's worth the effort. The right fit will completely transform your style. Choose clothes and accessories that are your right size, which will compliment you most.

Take the time to find your proper measurements. You don’t have to be a lover of fashion but at least you will have an idea of how you should look and it will take away the thought process of picking clothes; it will be a no-brainer.

The right fit will boost confidence, and create a sense of self worth and change the way others view you. Always dress for yourself but at least others will take you seriously, whether it’s in the work force, the dating world, or just around town.

About the author

Leonel Rojas

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