Why You Need To Be Wearing Properly Fitting Clothes

I’m sure even as you read the title you were thinking to yourself … No Shit! This is one of those pieces of advice that we’ve all heard a 1000 times and for some of us apparently, 1000 hasn’t been enough. I can’t count how many times I’ve seen guys wearing all the right pieces to have an awesome outfit but they wear items that don’t fit right and it throws off the whole look. In this men’s style guideline, we’re going to cover why wearing properly fitting clothes is a necessity to being stylish and how you can do it.

Men’s Style Guideline: Thou shalt wear clothes that fit.

This will be the first and arguably most important of the men’s style guideline series due to its relevance in every outfit. Hell, maybe the most important article on this site. So get your pens out and get ready to take some notes!


Properly Fitting Clothes Are a Necessity to Being  Stylish.

I don’t think there’s anything controversial about that statement. Plain and simple fit trumps all. Properly fitting clothes can completely redefine an outfit, highlight your proportions and drastically improve your overall style game.

Well, I talked the talk now let’s see some examples…


Properly Fitting Clothes Completely Change Your Outfit

The exact same shirt tailored down a size or one size bigger to fit you properly can change you from looking ragged to stylish just like that. Don’t believe me check out these crazy examples below!

Man wearing pink pinstriped dress shirt side by side, with one being tight and well fitting and one being loose and not fitting well
Here’s a great example from zipseam.com of how much difference the fit of a shirt can make in your style!
Man wearing poorly fitting white dress shirt with bad fit beside the same man wear properly fitting clothes like a dress shirt
Another great example of a badly fitting dress shirt and a properly fitting one side by side.








The difference in looks in the photos above speaks for themselves. Proper fit can either make or break an outfit.

I’d go as far to say that the fit of the clothes matters more than the brand

Yes, I know wearing Gucci is an awesome way to showboat your money, and that it has tremendously quality material and design. But in terms of looking well dressed, a quality properly fitting piece of clothing is going to beat out a poorly fitting more expensive product every time. Now, if we can combine them that’s the dream!

Fashion expert Tanner Guzy, Masculine-Style.com agrees with me

“Without proper fit, your clothing is going to look ridiculous. It doesn’t matter if it’s expensive material, the right color or season appropriate; if it fits like crap it looks like crap.”

So does well-known style blogger Brock McGoff over at The Modest Man

“Fit trumps all. When it comes to dressing well, nothing matters more than fit.”


Having Your Clothes Fit You Well is Going to be Crucial in Looking Your Best!


Properly Fitting Clothes Will Highlight Your Proportions

What does it mean to highlight your proportions?

I think photos are the best way to explain this.

Man walking down sidewalk wearing a well fitting white oxford shirt , with blue suit and white plimsolls
Properly fitting suit. Photo from lookastic.com


Man leaning against lamp post wearing properly fitting clothes like a brown henley shirt, navy jeans and brown boots
Properly fitting casual outfit.

Now, what did you notice in the above two photos?

You got it, they both have clothes that fit.

With the suit outfit, we can see a properly fitting oxford tight in the chest and arms showing off his physique. The pants are similar, perfectly fitting the legs. Now just because something is tight doesn’t mean it’s a great fit, it’s a fine balance. You want your clothes to fit snug on your body but not to look like they are suffocating you. Tighter isn’t always better! 

Similarly, in the photo below, we see another great example of proper fit. Now, this guy isn’t wearing anything special just a brown henley on some blue jeans with some desert boots. He, however, looks incredibly stylish because the all of the clothes fit great on him. The henley has the arms huggin’ the sleeves (Shout out to Chris Jones) with the jeans tapered to fit tight but not like spandex. This is a great example of a simple outfit that you could re-create for cheap which looks awesome because it fits well.

Okay, we saw properly fitting clothes now let’s see some bad examples…

man not wearing not properly fitting clothes like the blue oxford dress shirt which is too loose
Poorly fitting button-down


P.Diddy not wearing properly fitting clothes like the grey suit which is too big
Diddy in a badly fitting suit

The fit in the above examples leaves a lot to be desired and result in the outfits just looking off.

In the first picture, the dress shirt is clearly too big, ballooning out over his belt in addition to there being no definition in the chest or arms. The shirt doesn’t taper to his body and leaves him looking like a blob of blue. Going for a more tapered fit and probably sizing the shirt down would have this guy looking a lot better.

Finally, in the picture below, we have rapper P.Diddy wearing an atrociously poorly fitting suit. Yes, even celebrities like Diddy can mess up their style. First, let’s start with the pants. The pants on this thing look about 3 sizes too big. With a suit pant, you want a gentle taper and moderately tightness in the leg. Not touching the leg but not looking like you’re ready to go parachute diving either. The suit jacket is a little better fit, especially in the shoulder region. However, at the bottom of the jacket, we can see that it drapes too low and loses that tight figure. We’ll have a more specific suit write-up in the future, but needless to say, this is a bad example!

*Since larger and looser clothing was a style trend in rap at the time we’ll cut Diddy some slack.

How Can I Tell If My Clothes Are Fitting Properly?

This one is easy. Try it on!

Joey from friends trying on all of Chandler's clothes


I know it’s a pain trying clothes on but trust me it’ll be worth it. If it doesn’t fit you, it’s tough but sometimes you just gotta throw it out or ideally donate. I know, I know, it was your favorite shirt when you were 14 but it just doesn’t fit anymore, maybe keep t with your other sentimental stuff, but keep it out of your closet!

The same principles go for buying new clothes. Try them on to ensure a proper fit before buying!

Okay, Ryan, I get it, how your clothes fit matters. What should I do now?

There are 2 major things you need to do to have your closet full of clothes that fit you. Now, these steps are incredibly hard so brace yourselves.

  • Get rid of your clothes that don’t fit
  • Add clothes that do fit

Alright, maybe I exaggerated the difficulty a little …

When it comes to developing your wardrobe, it’s really not that difficult. The process, however, is a marathon, not a sprint. If you consistently swap out old poorly fitting clothes for new properly fitting clothes over time you’re eventually going to get there!

It’s really that simple! Next time you need a new pair of jeans, head down to the store and find a brand and fit which properly suit your body. Now, buy them. Finally, throw out that old pair of jeans which crushed your balls into your leg. That’s it. Rinse and repeat with your entire wardrobe and you’ll eventually have a closet of awesome fitting clothes. Obviously, if you have the money to spend, this turnover process can happen a lot faster. Along the way, you may find your size or fit changes as you gain or lose weight but keep calm, the same principles apply, just repeat the process.

Here are a couple tips I have used in my pursuit of the perfect wardrobe

  1. Throw it Out! If you haven’t worn it in the past year and it doesn’t fit you well, just throw it out.
  2. Don’t be afraid to try on clothes! It’s okay to try something on with no intention of buying it to see how a brand fits for future purchases (Also lets you order their clothes online for better deals!)
  3. Once you find a brand that fits you well, stick to it! You don’t have to only buy Ralph Lauren if it fits you, but generally, brands keep very similar sizing between their lines so you can be confident if you buy from them again you’ll have some consistency compared to a new company.
  4. Use a tailor! If you’re like me and your weight fluctuates as you gain and lose mass weight lifting sometimes getting a tailor to fit your more expensive clothes can save you a lot of money compared to purchasing a new product.

Here’s a great video by style guru Alpha M. on how to keep the clothes you already bought looking their best!


It doesn’t matter if you’re at the gym in a stringer, on a date wearing a button down or selling a big client wearing a suit, fit matters. The principle of wearing clothes that fit is going to have you looking better, feeling more confident and making you more likely to succeed at whatever it is your doing!

Changing your wardrobe to be filled with properly fitting clothes is going to take time. Slowly getting rid of clothes that don’t fit and replacing them with ones that do, however, will definitely be worth it!


This is might be the most important of the Men’s Style Guidelines. Wearing properly fitting clothes is crucial to looking your best!