The Crucial Style Mistake That Ruins Your Look From the Get-Go

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.

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 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

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.


  • 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 / Jeans

Here’s how your pants and jeans should fit:

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

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 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?

  • Larry says:

    Didn’t know any of this. Thanks.!

  • BlackQueen2012 says:

    At this point, mens fashion has gone so off the wall that it’s time to get back to basics. It always seems to go from one extreme to another – extremely baggy to extremely tight (now, I’m not talking about any of the recommended styles in this article which are to me reasonable enough). The classic regular (uniform like) fit has got to be pushed to that men learn to fit their clothes properly – I feel it is the only way to sort this mess out.

    When proper standards have become re-established, then generous and trim alternatives can be brought back in. That said, no matter the style, the clothes have got to fit properly and must suit the various male shapes. The fit needs to be redefined as ‘The Cut’ which pertains to the body shape (slim, tall, average, petit, longline etc), and ‘The Effect’ which pertains to the amount of give in the fabric – ‘Tight’ (for specific sports etc. only), ‘Trim’ (relatively close but not tight), ‘Regular’ (uniform like), ‘Generous’ (more relaxed but still fitted), ‘Loose’ (generally for leisure/lounge wear only).

    We men have learned to use a scissors and sewing machine – now it’s time for tailoring lessons.

  • Francis says:

    Hey bob, what a great article you have in here! .. my prob is not about the fittings which I am familiar with the do’s and dont’s.. it’s about my body type.. every year my size changes from small to medium and medium to large, then back again from medium to small for the span of 1 year. My body keeps changing so I have clothes with a set of small, medium and large and it’s very hard for me to invest on dress… any advice?

    • Robert says:

      Hey Francis, I wish I could help you, but I’m afraid I don’t have an answer for you there. I’ve never heard of someone going from a small to a large and back again each year, and wouldn’t know how to solve it except buy clothes for multiple sizes. That sounds very frustrating indeed.

  • Dp says:

    Are chuck taylors appropriate for a guy in his mid 30s? I don’t want to look like a teenager

  • Puneet says:

    Hi Robert,

    Great article! And great job with the prompt responses.

    My height is 5.8″, the suit jackets that fit me at the chest are sized 52 (European) / US size 42, however these sizes are for much taller people thus a bit long for me. I am afraid if I get them shorten by a tailor then probably it will look odd?

    Is there any other solution then getting a custom fit suit, which are pretty expensive or the alteration by a tailor to shorten the length would not make the the suit jacket not too odd?

    Thank you very much in advance!

    • Robert says:

      Hey Puneet,

      you have a rather difficult problem that doesn’t have an easy fix. Your instinct that getting the jacket shortened looks a bit odd is right. You can get them shortened a bit, by a reputable tailor, but it’s likely to throw off the balance of your jacket.

      Where exactly does your jacket end?

  • othman says:

    i am very skinny guy and i have found that i have kind of hourglass body , and my problem is to find the perfect White dress shirt that fits me . i need your help !!

    • Robert says:

      Well, I certainly feel your pain!

      The thing is, finding the perfect-fitting dress shirt off the rack is nearly impossible. You should always count on having it altered by a tailor. Just try the find the closest-fitting shirt, and then get it altered.

  • Mayur Sharma says:

    My thighs are thicker. Height 5’8.Which size of jeans suits me. Regular or slim fit??

    • Robert says:

      If your thighs are thicker, you’re probably better off with a regular fit. You might actually have to go a size up and then get it taken in at the waist.

  • David says:

    Robert, Just came across this article and it was a lot of help. I recently lost over 50 pounds and had to revisit my wardrobe as a lot of my clothes were simply too big and suits couldn’t be altered enough to fit. One question I have come up with is where exactly should dress pants fit around the waist? Is it still at the navel or an inch below or what do you recommend? Also, pleats or flat front?

    • Robert says:

      Good question, David. It’s actually a matter of taste. Some guys (especially traditionalists) like to wear their pants high at their waist, while others prefer low-waists.

      As for your second question, I’m not a big fan of pleats, so flat fronts.

  • Michael says:

    Hi would black joggers white vans and a dark red volcom shirt look compatible or what do you think I should alter?

    • Mikey says:

      Would gray pants white vans and go better with a dark blue Cali life shirt or a black shirt ?

      • Robert says:

        @Michael: Color-wise, that should work. But I wouldn’t suggest you wear joggers outside of your house.

        @Mikey: They would both look fine, color-wise.

  • D says:

    Hi, I always had hard time finding right fitting clothing. I’m a 5’8 male, and weigh 240 pounds. It don’t help ether that I have barrel chest and thick short neck. Everything I wear, is ether to tight or baggy. And I don’t have luxury to afford a tailor. I would like to know if I even could find clothes that fit me correctly?

    • Robert says:

      Hey D, I’m afraid finding well-fitting clothes with your body-type will be extremely difficult if you don’t want to invest in tailoring . It’s hard enough for us with with a more regular body-type.

  • Jacob says:

    I recently choose to do a speech on ties and loved the instructions you gave. I found a knot named the “Ellie knot” and hoped that you would provide instructions that I could print out and use in front of a mirror. Thank you for all of your great works. Please e-mail me if you do.

    • Robert says:

      Hey Jacob,

      thanks for your comment. While the Ellie knot does look pretty cool, I try to keep my advice basic and simple here. So with that in mind, I don’t think the Ellie knot would really fit.

  • A says:

    Hi – I just stumbled on this site looking to upgrade my wardrobe. One question I have on pant fit is not covered in your tips: thigh ‘tightness’ and crotch. How tight or loose should thighs be on good-fitting pants? Also for the crotch, I like a little more room. Is this alterable at the tailor? What’s appropriate fit?


    • Robert says:

      Hey A,

      it’s a good question. You want your pants to fit snugly in your crotch, but not too snugly. You don’t want to be showing off your bulge ;)

      Same goes for your thighs. They should fit snugly, but you should have enough room to comfortably move around. The fabric shouldn’t feel like it stretches whenever you end a knee.

      Hope that answers your question!

  • Kishan says:

    I’m 5’4″ height and somewhat fat
    My neck is short as I had a surgery
    How should I get better???

    • Robert says:

      Hey Kishan,

      I’m not sure I understand your question. Do you have trouble finding the right fit?

      If that’s the case, you might need to look into having a tailor alter your clothes a bit. This is something all of us have to do to get the fit exactly right, but when you’re an unusual body-type, it tends to be even more important.

  • Listography I: Fashion Faux-Pas Part 1 | UP TO THE NINES says:

    […] Restart Your Style […]

  • Preston says:

    Would wearing dark jeans with converse and a navy blue and red plad shirt with a light denim button up go good together

    • Robert says:

      Hey Preston, it sounds like it should work. Though, I’m not really sure what you mean. I wouldn’t wear a denim shirt over another shirt. A denim jacket should be fine.

  • Raza says:

    I have a black shirt with purple stripes. I was wondering which pant colour would look compatible with it?

  • Jacky says:

    Thanks Rob! It’s really helpful for a total beginner like me. I’ve always been the guy with low self-esteem and trying to make a change. Keep it up and more to go !

  • gio says:

    Great advice, It’s like having discovered a whole new world!

    I loved the article and already subscribed -I am a fun and smart guy inside but that wasn’t coming across on the outside, so I decided taking over myself by going for a so needed change and actually just went shopping… twice… pity I hadn’t found your blog two weeks ago sill I think I did ‘just ok’ ;)

    I just find myself lost when shopping, I can get a cool t-shirt and nice jeans separately but when it comes to put an outfit together… man I block. Not a nice feeling and kind of frustrating because matching colors is a nightmare and that’s actually what I’m looking for, to have more color in my wardrobe… I really like would like to achieve a trendy look that’s not over the top

    Anyway I am loving your blog!

    • Robert says:

      That’s exactly what we’re aiming for here at RYS, Gio — a stylish look that’s not over the top.

      • Rob says:

        It is easy advice to follow if your body shape is fairly standard or you happen to be a good match for whatever this seasons style is. For people like me it is almost impossible to find clothes that fit well unless I get them specially made.

        I have big thighs. I always have. Even when I was at my thinnest and had a 31″ waist, the legs on size 31 pants were usually too tight to fit it. I also have a very broad chest and shoulders. The only way to fit into a designer suit is too go several sizes up and there is only so much they can be adjusted. Designer clothes tend to be a tighter fit to begin with.

        This season (winter 2014-2015) seems to favor even tighter fitting pants than normal. Skinny jeans for men and running tights are everywhere. I literally can’t find anything to wear. T-shirts, pants, sweat pants are all rediculous.

        The problem isn’t that men don’t know or don’t care about how clothes fit, it is the stupid designers who think that everyone is a 6 foot plus skinny model who wants to dress like a woman. If they made clothes that for well for me, believe me, I would wear them.

        • Robert says:

          Yeah, Rob. I know there’s some body-types that are a lot harder to find suitable clothes for, and there unfortunately isn’t an easy solution for it.

          Unfortunately stores still only sell clothes in a one-cut-fits-all style, and we all need to make some adjustments. I can’t buy any shirt off the rack either without getting it slimmed down.

          But yeah, I know some guys have it harder than others, which is a rotten shame!

  • Mary says:

    I thought the first pic, of the guy with a suit, one too big and the other supposedly the right size- the ‘right’ fitting suit is just too small on him. It doesn’t button properly in the front. The tie is showing where it’s supposed to be hidden after buttoning. Not correct. The pants fit like stovepipes. They look restrictive. While the over-sized suit is two sizes too big, the second suit looks too small.

  • Dave says:

    These are some good tips. Just found it on Google. My problem is that I am tall and somewhat on the slim side. Most everything I own is XL for arm length, but I get that billowing/flying squirrel webbing from my arms to my hips, which I think is my biggest problem. I accidentally bought a “slim” dress shirt recently, and wow what a difference! You’re absolutely right, it is about fit. When I get a new job, my plan is to chuck all of my current wardrobe and start building one where the clothes fit. No more pleats. No more “loose fit” jeans/khakis that puddle at the ankles. No more rounded toed shoes. I need to find a good store that sells affordable slim fit dress shirts.

  • parameshwar says:

    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 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!!

    • Robert says:

      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.

  • parameshwar says:

    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

  • Jason says:

    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.

    • Robert says:

      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.

  • Harry says:

    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.

  • Joshua says:

    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!

  • Benson says:

    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.

    • Robert says:

      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?

  • Rob Leonardo says:

    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. :)

  • Brock says:

    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!


    • Robert says:

      Thanks Brock. You took the words right out of my mouth. Expensive clothes aren’t worth the money if they don’t fit you.

  • Chin says:

    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.

    • Robert says:

      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.

  • Izzy says:

    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.

    • Robert says:

      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.

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