You probably make this 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 it. You’re so used to making this mistake, you’re blind to it.
You keep wondering why clothes don’t look as good on you as they do on others, and it’s 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 style bloggers sharing their most important tips for novices, you probably noticed that several of them mentioned fit.
It’s something that I was expecting, since the fit of your clothes for a large part determines how an outfit looks on you.
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 they 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
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.
T-shirts
- 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.
Shirts
- 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.
Pants / Jeans
-
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.
Jackets
- 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 shirt 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 shirt 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?

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 I’ve started regularly pruning my closet.
You should do the same.
It’s a great kick to really be able to compare your past style to your reinvented style. It’s a real boost in confidence to see how much you’ve really improved.
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.
And if someone as awesome as myself can forget to check these things, anyone can. 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. It will astound you how such a basic fix can have such a drastic effect on how you look.
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? Let us know in the comments!





Hey guys, I'm Robert, and I used to be a terrible dresser. But after a long time trying to make sense of personal style, I now walk out my door every day, looking (and feeling) my best. I want the same for you, so I'm here to simplify the process.
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hi,its parameshwar again,i bought something like a chino brown in color(stress on the something!).i teamed it with a grey v neck tee& a white shirt,it looked awesome but i have a strange feeling that it is NOT a chino b’cause its smooth,tight fitting and sort of elastic.so the big question is whats the characterstic feel about a chino and what did i buy??
do reply fast as i have a class reunion lined up in 3days!!
Can’t tell from the description what it is, but chinos shouldn’t be elastic. I can tell you that much.
And chinos shouldn’t be tight, they should fit you closely, but not tight. You shouldn’t feel restricted in them.
In fact, nothing you wear should ever feel tight.
First of all, AWESOME website!!kudos for it.
im 16 and all the shirts which i have billow near my sides! i just hate them billowing,i have a slight flab in my belly & a slightly arched back,is it responsible for it??? DO HELP.
and could you just explain this-”"The front of your pants leg should have a slight break, where it meets your shoes.”",thanks tc
Thanks Parameshwar!
Your body isn’t to blame — your shirts are. You need to have them taken in at the waist by a tailor. Seriously, just try it with one, and see the result.
Check out this Primer article for more info on pants break: http://www.primermagazine.com/2012/learn/how-pants-should-fit-the-principles-of-fit
when I buy button up shirts I make sure the shoulders rest properly and the end at the proper place at the wrist (I think…what is the dimple of the wrist? where the wrist and hand meet?) My problem is the billowing at the waist and most especially in the back area. I am 5;10″ and weigh 180. My waist is 32″. This seems pretty average to me in the traditional sense, but for some reason I find it hard to find good fitting shirts. Any suggestions on brands that may work better for me? I am toying with the idea of having shirts tailored for me but that can easily become an expensive endeavor.
Hey Jason,
I have the same problem with the billowing at the waist. You might try looking for slim fit shirts, but you definitely should also try the tailor. The cost is sooo worth it. Just try it with one shirt and see the difference it makes.
Oh, and the dimple of the wrist is where your thumb bone meets your wrist bone. You have a small dimple there.
Hope that helps.
Since I’m 12 I and size 12 I buy close size 14 because I want to have them longer. And for shoes I get size 6.5-7 and I’m size 5. What I do is stuff something comfortable in the toe like a lot of cotton balls or something. It may sound silly but it works.
Why do you want your clothes longer?
Thanks for all the advice! Found you via RealMenRealStyle, and I’m digging it! My problem has been a lack of choice in clothing (being 6’9″ and thin, it’s hard to find fitting clothes). I generally end up buying clothes that are too wide/spacious without being long/tall enough. I’m going to be keeping a closer eye on fit as I restart my wardrobe. Thanks again!
Yeah finding the right fit for your body type can be a real pain, but it’s something you should never settle on.
Don’t get me wrong but why on earth these do & don’t are in words everywhere. Why it’s so hard to find them in pictures?
After all…A picture is worth a thousand word.
That’s a valid comment, Benson.
I’ve found it is quite hard to find a picture on the web to show exactly what you mean.
Maybe I’ll work on some illustrations to accompany this article in the future.
In the meantime, is there anything specific you need clarification on?
OMG! I’m guilty as charged! Nice blog you have Robert! This is a good substitute for Men’s Health as they seldom do this thing.
Thanks Rob!
Great post, Robert. Fit is definitely the most important aspect of style…for anyone. I’d rather have a handful of cheap outfits that fit perfectly that a closet full of expensive ones that are too big (this happens to be my most common problem).
Keep it up!
-B
Thanks Brock. You took the words right out of my mouth. Expensive clothes aren’t worth the money if they don’t fit you.
Can I post your post to my wordpress blog? I’ll add a one-way link to your forum. That’s one actually nice post.
Thanks Chin. You can post about this article on your blog, but I’d actually prefer it if you’d only post a snippet of the whole article.
Yo Robert,
Great article with super practical tips man.
I am really learning some great stuff from this. Fashion has always been one of those things that I have always felt “I am just bad at”. I like reading your content because it is helping me recognize 1) the mistakes I have made and 2) how to fix them.
With my body style a lot of clothes makes me look like a beefcake (way too bulky).
But I hate this look, so I actively try to avoid it. Reading this article helped me recognize that since I hate that look so much that I often buy clothes that is too big for me.
Thanks Izzy,
that’s a great comment!
I love that the first guy to comment here doesn’t really fall into any of the 5 types I mentioned :p
Seems to me like you’re an anti-showoff. You hate the show-off look so much that you go too far in the other direction.
Know what you should do? If you have a couple of shirts that fit well on the shoulders, take them to a good tailor. Ask him what he can do to improve them.
When he’s finished, note how well the clothes compliment your frame. It will be a worthy investment.