How Should a Dress Shirt Fit? Your 10-Step Checklist

bad fit example
How a Dress Shirt Shouldn’t Fit

If you want your shirt to look good on you, then you have to know how a dress shirt should fit.

Getting the fit right is critical.

Without the right fit, you can get everything else right, but you’ll still look like crap wearing it. Without the right fit, you got nothing.

So how should a dress shirt fit? Do you know how to check?

The information you can get about it is often vague, it can leave you with questions, and it often comes without visuals.

Well, today I’ll give you a sample from my e-book — Style Made Simple — that will show you ten different ways to check if your shirt has the right fit, so you never have to wonder again.

The Difference Fit Makes

I can keep telling you how important fit is, but I thought pictures would tell it better.

Just  look at the difference between these shirts fit, worn untucked and worn tucked. You’ll see the difference between a dress shirt in the right fit and when a dress shirt’s too big.

Shirt fit untucked
Shirt fit tucked Shirts like the white one are only useful when your girlfriend’s into pirate role-play.

Now, you may think the white shirt’s fit is an extreme example of bad fit, but you’d be surprised how many guys are walking around in similarly ill-fitting clothes.

Hopefully that doesn’t include you. But if it does, we’ll fix that today.

The Perfect Fit for Dress Shirts

Before we move on, you need to know that off-the-rack shirts are nearly impossible to find in your perfect fit. Something will always be off.

When the sleeves are perfect, the waist is too baggy. When the waist is perfect, the chest is too tight. When the chest is perfect, the sleeves are too long.

You should count on something always being off. Because otherwise you’ll end up wasting too much time trying to find that perfect-fitting shirt. And you’ll still be unlikely to find it.

So, How Do You Get the Perfect Fit for a Shirt?

You need to ensure the shirt fits in three key areas — chest, shoulders and neck — and then try to get as much right as possible.

The rest of your shirt can be easily altered by a tailor, and won’t cost so much. But your chest and shoulders are mostly unalterable. And collars can be altered, but it’s hard to do without ruining the shirt, and thus costs more.

“But can’t I just use the money to buy another shirt?”

Yeah, you can. But like I said, perfect fit is nearly impossible to find. So if you use the money to buy another shirt instead, you’ll just end up with two ill-fitting shirts instead of one that does fit.

And if that still sounds like a better deal, then you need to cram this into your head:

One shirt that fits is worth ten that do not.

Ill-fitting shirts are worthless. They’re garbage.

You’re not getting two shirts for the same price as getting one and having it tailored. You’re getting two pieces of crap.

They’re not worth the money, unless you get them fixed.

And if you find a shirt that fits everywhere, except the waist or sleeves, then getting those altered can be done for a very fair price.

Shirt Fitting Guide: How Should a Dress Shirt Fit?

So when you’re in the store, trying your shirt on, what do you look for? How do you determine the shirt is worth your money?

The checklist below will show you how to tell if a shirt is too small or too large.

Here’s what you do:

1. Check the shoulder seams first.

They should rest at the edge of your shoulders. Not on top, and not over them.

shoulder seam illustration
If your shirt fails here, no need to check the rest. It’s doomed.

2. Check the buttons

Are the buttons pulling at the fabric to try and reach each other?

Is the fabric of your shirt coming apart between the buttons?

Bad sign! Your shirt’s too tight.

Left: Shirt is too tight. Right: Shirt is fine
That should be obvious, right?

3. Put two fingers between your neck and your collar

If you can’t fit two, the collar is too tight. If you can fit more than two, your collar’s too large.

collar space
Index and middle finger, guys. Pinkies don’t count!

4. Hold up your left arm, and pinch the fabric together at your sides

You should be able to pinch around 2-3 inches. Any more than that, and it’s too large. Any less and it’s too tight.

Left: Way too much room. Right: Perfect
Note how the left picture also looks more depressing. Bad fit at work, guys..

5. Feel how much room you have in the sleeves

Are your dress shirt sleeves too baggy? You don’t want to have too much excess fabric in your sleeves. They should be tight, but not too tight. You should be able to bend your arm without feeling the fabric stretch. Armholes should be as high as possible without restricting movement.

illustration of proper armholes
Also important when your shirt isn’t see-through.

6. Check your dress shirt’s sleeve length when you let your arms hang by your sides

How long should your sleeves be?

Sleeves should end by your thumb dimple. If you don’t understand where your dimple is, glide your finger across the side of your wrist, and feel for an indent.

Thumb dimple
Sidenote: If any of you are looking for good hand-models, I’m available.
different lengths of sleeves
Left: Too long. Middle: too short. Right: As it should be.

7.  Raise your arms in front of you

If you feel the fabric stretch in the back, the shirt is too tight.

Arms raised in front
If you were turned into a zombie, would the back of your shirt survive?

8. If you plan on wearing your shirt tucked (some or all of the time), tuck it in when trying it on. Raise your hands above your head and see if it stays tucked

arms raised position
Ballerina pose optional. When in company, I suggest a double fist-pump to protect your masculinity.

9. Pretend to tie your shoelaces, and see if the shirt stays tucked 

Bending over
You could also pretend to drop a quarter. Totally up to you.

10. If you plan on wearing the shirt untucked, raise your arms and make sure none of your belly is exposed

Arms raised position, belly showing
See? The left guy’s so embarrassed he can’t even look at you.

Side-note: You can perform these checks at the tailor too, before he gets to work on your shirt, and make sure he doesn’t make it too tight.

Now Go Find Some Well-Fitting Shirts

You now know how dress shirts should fit, so go get some. And don’t forget to check the shoulders, chest and neck first.

And, before you go on a shirt shopping-spree, check your wardrobe. Maybe you already have a few shirts that fit in the key areas, and you can get them tailored into perfection.

Wearing a great-fitting shirt will make you look and feel so much better. You won’t even believe what wonders it does for your confidence.

Prepare for many compliments.

And if you’re interested in getting more advice like this, then you want to get on the launch list of my upcoming e-book: Style Made Simple. Sign up below for more information and more free samples.

  • Indiana Jones says:

    Really Helpful. Thanks bro

  • adam says:

    I bought 15.5 32/33 it fells a little tight a little lately lol I need to buy 16 32/33 now would it Sleeves get a little bit longer

  • me says:

    Not even a guy. But the guy in the pictures is sexy..

    so here I am.

  • Adrian says:

    Many thanks for this info, Robert! This has helped me a lot. I will always keep these tips in mind whenever I plan to buy shirts! You’re a blessing to us lol! Take care!

  • Mike Sanders says:

    Very useful infos thanks! Look, I’m slim and when I try shirts I usually have problem with neck and my neck is slim too and as a matter offact I can easily insert three fingers while all other checks in the list are okay, is this okay, or the neck should be priority? Thanks!

  • Jose says:

    Okay so my height is 5’10” and on step 10 when I do that on calven Klein polo shirt you can see my belly and that was large so I got xl and did the raise my arms up and you could still see my belly I definitely know I don’t wear a 2xl because that would look to baggy on me can you help me please

    • Robert says:

      Hi Jose, this article is more regarding button-down shirts rather than polo-shirts. With polo shirts, instead of raising your arms above your head, raise them sideways so they form a 90 degree angle with your body. If at that point, your belly still shows, that shirt isn’t a great option for you.

      It doesn’t mean you should go a size larger. The size isn’t the issue. It’s the cut of the shirt that’s the issue, and going larger will likely make the shirt fail some of the other checks in this list.

  • rafi says:

    Informative article.

    What about unbuttoned vs buttoned sleeve length? In test 6, I assume you are referring to length when buttoned at the wrist. Unbuttoned lengths are often recommended to be longer to avoid the shirt riding up your forearm when your arm is extended (as seems to have happened in the photo for test 7). However, it also may turn out that the excess length will cause some billowing at the forearm when the arms are down at rest. I guess that there’s a trade-off here.

    • Robert says:

      Yeah, ithere’s no avoiding the shirt riding up your forearm completely. If your stretch out your arms in front of you, or sideways, the sleeves will ride up a bit. That’s normal. But as long as they hit your wrist dimple when they hang by your side, you’re good.
      And yes, you want to measure the length while the shirt is buttoned, though, yeah, it shouldn’t make that much difference. You DO NOT want billowing at your wrist.

  • Brian says:

    Robert,

    I recently bought some shirts sized 15.5 X 35, slim fit. The waist and sleeve length are perfect. I’m very happy with the fit with my arms down, but when I put my hands in front like a zombie, it stretches in the back and gets tight in front of my shoulders. This particular brand has slim, fitted and classic cuts. I would say the neck is just a tad snug (by about a half size or less), but I also have heard that when you go from a 15.5 to a 16 neck, the over all size essentially changes from a medium to a large. And while I’m tall, slim but relatively proportional (6’2, 185 lbs), large is always too big in width. These are mail order shirts, so I am trying to decide if I should return them and try 16 neck size slim fit, or 15.5 neck size fitted fit. What would you do?

    • Robert says:

      It’s hard to find a perfect fitting shirt off the rack, so most of the time, it requires some adjustments from a tailor. Are you wearing this shirt with a tie? If not, then the neck doesn’t matter as much — you can just leave it unbuttoned. Otherwise, the best option might be to try the larger shirt and have it taken in and the sleeves shortened.
      But before you do anything, just try the 16 neck size and see how they fit.

  • Rubén Lara says:

    Hi Robert,
    It’s an excellent and easy of understand article. Thank you very much for it.

    One question, sometimes I’m in doubt with my customers when they have a muscular body.
    Medium size is always fit and small but Large is not fit.

    Only full custom shirts is the option for this body type?

    Best Regards
    Rubén Lara

  • Jessica says:

    My husband is 6 foot 8 and about 265 lbs. We’re struggling to find dress shirts that are long enough. Any advice? We’ve tried XXL and XXXL in classic fit and slim fit but they still don’t pass the raising arms test. For now he keeps his blazer on.

  • Irving says:

    I would to follow your information in order to dress better and share with younger males that I am around.

  • Bryce says:

    Should you wash a shirt before taking it to the tailor…to account for any possible shrinkage?

    • BlackQueen2012 says:

      I’d definitely give that a yes! In fact, I’d do it after a few wears so to be sure that any shrinkage has stopped – see what Robert says….

  • Joe says:

    Is #5 something a tailor can fix? I often encounter resistance from shirts when I lift my arm up and it’s because the armhole is too low.

  • BlackQueen2012 says:

    While I agree that the white shirt is too loose, the blue one is IMO too tight – it just looks like an old shirt that has had too many washes and needs replacing. I think the fit should be something between the two above examples except that I’d be a little more cautious with the volume of fabric around the waist – you still need a little more give in that area though. I know you don’t like your sleeves too long, but why not go for short sleeves an inch or two above the elbow (or roll up your sleeves half way) – I saw you in previous examples and you’ve good arm length, so you may as well show it off.

    • Robert says:

      Well, we’ll have to agree to disagree on the blue shirt.
      And I do usually roll up my sleeves, but for the purpose of this article, I left the sleeves down to show where the sleeves should end ;)

  • varun says:

    i am an Indian boy who is struggling to get a right sized shirt.help me the 38 size do not fit me and 40 is a little bigger, what should i do ?

  • Fred says:

    So richly detailed. Way to drill down! Wrist dimple works. I will never buy a shirt with a “34/35 sleeve.” Does this annoy other men too? Companies sure love these tags. They double their customer base with this one slick maneuver. Do not fall into this trap. It’s one or the other! 35 is always too big for me. I hate that line extending beyond my shoulder. It’s become a bad omen. That extra inch of material is a huge nuisance and always gets in the way. I’m constantly rolling up the sleeves, which leads to more discomfort. 34 or bust.

  • Brad says:

    Shopping in Melbourne on a trip from New Zealand. These tips just helped me buy 3 reasonable value 100% cotton long sleeved shirts with more confidence. I was struggling and the woman in the store nearly made me go for a medium but the shoulders were tight and the buttons pulling a bit! U saved me! Thanks

    • Robert says:

      Hah, that’s awesome! I feel like a superhero :)

      • Jose says:

        Okay so my height is 5’10” and on step 10 when I do that on calven Klein polo shirt you can see my belly and that was large so I got xl and did the raise my arms up and you could still see my belly I definitely know I don’t wear a 2xl because that would look to baggy on me can you help me please

  • KP says:

    I am a 5’7″ guy with (I believe) a shorter lengthed body as well. Many shirts I want to wear more casual (untucked) hang too low past my waist; to the lower part of pockets. Overall I am a medium in body. Any advice?

    • Robert says:

      Sees like an obvious answer, but you might consider tucking them in. For short guys, you don’t really want to make your legs appear even shorter than they already are.

  • Jill says:

    Single mom here I have 4 kids only one boy,he is nine. My sons shirts are tight on the neck and if I get one that fits him on the neck he ends up swimming in the rest of the shirt. Do you have any hacks? Any hints, tips or tricks are greatly appreciated. Thanks.

    • Tom says:

      Look into collar extenders. They let you buy the shirt that fits correctly in the body, while expanding the neck slightly.

    • Robert says:

      Sorry Jill, I don’t really deal with boy’s style and don’t have a hack for you. For a grown-up, I would’ve suggested tailoring. You might try Tom’s suggestion though.

      Otherwise, consider just leaving the top button unbuttoned.

  • Noah says:

    My shirts fit me everywhere, except when I raise my hands over my head, the shirt un-tucks and the result is similar to a muffin. I have visited the local taylor and she said that I needed a bigger shirt. If I go bigger, then the rest of the shirt does not fit me correctly. I have a tall and slim body type. My current shirts are 15 1/2 34-35 slim fit. What would you recommendations be? Thank you!

    P.S. I am a salesman so my appearance is very important to my career.

    • Leslie says:

      See #5. Armholes should be as high as possible. I have tailored shorts have higher armholes don’t have this problem. RL standard/classic fit has this problem but the slim fit doesn’t because it’s armhole are 2 inch higher. So you don’t need a bigger shirt.

      Good luck.

      • Robert says:

        Thanks for pitching in, Leslie. you’re absolutely right.

        Going bigger is definitely not the answer. That’s bad advice! In fact, it would likely make the muffin-look even worse.

        Of course, your shirt will always come untucked a little when you raise your arms over you head. With higher armholes, it just won’t do so as much.

  • Joel says:

    Great guide! Do you have a similar one for how the suit/suit jacket should fit?

    Best regards

  • Jack says:

    Good article. I’ve never seen it broke down like this before. As a tall skinny guy I’ve always had the problem of my shirt looking like a box around the waist.

    I’ve always bought real cheap work shirts, but recently decided to splurge on an expensive shirt because I figured I’d try a nice quality fitted shirt for once. What convinced me was the fact that the company’s shirts are made with ranch work and horseback riding in mind (which I do) so length is a bit longer than normal and they are well built. A shirt sized down from normal by these guys fits me perfect in all areas except the sleeves which are just very slightly short, and the shoulders are barely within tolerance according to your picture. But I can live with that since it looks great and I always roll my sleeves up anyway.

    With that said, I’d like to echo what you said about confidence. It really is a big boost to your self esteem to be well fitted, and exponentially so when you receive compliments. I’ve definitely started to pay more attention to detail in other areas as well, but I reckon the shirt is the most important to get right.

    • Robert says:

      As a tall skinny guy myself, I know where you’re coming from! And yeah, I often accept slight sleeve discrepancies on my casual shirts, because I always roll the sleeves as well. Great minds think alike!

  • Jack says:

    What does it mean when I have fabric bunching up at my shoulders when I raise my arms parallel to the ground?

    • Robert says:

      I’m having some trouble picturing it, Jack. Could be that the armholes are too wide. But then, there will always be a bit of bunching at the shoulders when you raise your arms. It’s hard to tell without actually seeing it.

  • Philip Zeitz says:

    My problem is in the shoulder area where the line goes beyond the point it should. They seem to all fit that same exact way. You said stop if the shoulder area is incorrect. How do you solve this problem if all of them are this way?? Thank you.

    • Robert says:

      That would be an annoying problem to have, but you should be able to find some variation among different brands. Otherwise, have you tried going down a size?

  • Dan says:

    If I send you a picture of me wearing my shirt, can you tel me if its too tight and short?

    • Robert says:

      Have you tried the tests given in the article? If you go through the checklist, you should have your answer ;)

      • just saying says:

        but you just telling him is way faster

        • Robert says:

          I’d have to disagree. You can do these checks in less than a minute. Taking a picture, sending it to my e-mail and waiting for a reply would take much more time.

          Besides, I can’t as accurately tell the tightness of a shirt from a picture as you can tell it by feeling. I can’t tell from a picture whether the fabric stretches when you move around or whether it restricts movement (unless the shirt is WAY too tight, in which case, you shouldn’t have any doubt).

  • Stephen says:

    I really enjoyed going through your staff. I think you are hitting it on the nail. Keep it up its an excellent work.

  • Brian says:

    Well put together stuff Robert. Cheers. It’s nice to see something that gives some proper visual aids. I work a bit with tailored shirt companies myself that cater to bigger guys, primarily gym buffs and bodybuilders so the most common issue: big shoulders, small waist.

    For some guys it’s practically impossible to get anything that doesn’t look like a tent from the bottom of the chest down. In fact I did a post on it recently if a link can add to helping any of the guys on here https://www.shirtswithbuttons.co.uk/blog/finding-fitted-shirts-for-bodybuilders/.

    Personally though, I struggle most with fitting the tricep. I have shorter thicker arms so it’s often a case of baggier shoulder or longer sleeve for more upper arm space. You recon there is a better fix on this one though?

    • Robert says:

      Thanks for the comment, Brian. I’m sure some readers will find this helpful!

    • Victor says:

      Brian,

      After years of suffering off the rack shirts that do not fit except one area at a time, this year I ended up ordering made-to-measure shirts from online tailors. Average price costs me about $90 per shirt, but it is all customized to my sizes. This is the way to go.

  • David says:

    Should I wear a t-shirt underneath a shirt? casual wear and business?

    • Robert says:

      Honestly, opinions are divided on this issue. Some people swear by wearing an undershit, other people are the opposite.

      Personally, I sometimes to and sometimes don’t. Just make sure your t-shirt doesn’t shine through ;)

  • yellow hoodie says:

    Good blog post. I certainly love this website.
    Continue the good work!

  • Wesley Lovell says:

    I’m still uncertain on whether my shirt is too small or not, I find it a bit of a nuisance having to pull my shirt down every time I get up from a sitting down/lying position (I haven’t really taken notice before now so I don’t really know if this is just normal with a normal fitting shirt or not) and the area below the bottom button opens up by about 3 inches when pulled it down.

    The problem is that i’m slightly overweight so it may be the cause of this little problem I have so therefore would it better for me to go for the next size up or could losing a bit of weight solve the issue?

    • Robert says:

      Hey Wesley,

      it’s really hard to tell without actually seeing it, but it does sound like your shirt might be a bit too tight. Losing weight will probably solve the issue, but you might also try finding shirts that have a bit more room in the waist. Going up a size might make your shirt too large, which also doesn’t help.

  • Madhav Sekar says:

    Never had any one break it down like this for me, not even tailors. Come to think of it I don’t even think my last tailored shirt met all these criteria.

    I’ll be sure to bring these tips with me next time I go to get a shirt.

    Thanks for the great tips!

  • Dave says:

    How far down should the shirt go in the front? Both t-shirts and button ups when wearing untucked.

  • Toby says:

    Great article, Robert. I know this guide is for shirts but I applied it to the t-shirts I wear and I realise I’m wearing a size too big. I should know better at 36 years old but I always thought having a slightly baggy t-shirt lets air circulate better but mine seem to make me sweat more. Even within 30 minutes of showering.

    I bought a couple of smaller t-shirts the other day, “M” instead of “L” and they fit almost perfectly (just a slightly tighter feel around the neck) and I can go the whole day without sweating and making them smell.

    I still don’t quite understand it. Whether I’ve just had my old “L” size t-shirts too long and the smell is ingrained or whether it is just the size (when I pull the excess material out to the side I could fit another half of me in, lol! And the underarms do that tenting out thing). Ohh and as your guide points out, the seam on my “L” t-shirts “falls off” my shoulder.

    I look forward to having a complete, long-overdue, clear out of my wardrobe this year. Now I know what to look out for when I buy some new shirts, cheers :)

  • Bob says:

    Is the sleeves are too long can they be shortened and is this an expensive alteration? Thanks, great article

    • Robert says:

      Hey Bob!

      Your sleeves can definitely be shortened, and it shouldn’t cost too much.

      The exact price will depend on your location and which tailor you attend, but it should be around $15-$20.

  • DannyBlue says:

    Very informative article, thank you. Which off-the-rack shirts are you talking about, is it supermarket, high-street or designer kind? Because I totally agree that basically all off-the-rack shirts look like parachutes around waist, but I had a good experience with BOSS, Z Zegna and Armani collezioni. BOSS being the best value for money as their color, material and stitching is most durable. But these brands’ shirts are in USD 150-200 range so for basic everday shirt (especially when worn under suit) it may be better to buy something well-made but cheaper and baggy, and then have it tailored, right?

    • Robert says:

      Thanks, Danny.

      I would recommend anyone just starting out to invest first in cheaper shirts, and make sure they know what they’re doing, before they invest in super-expensive, top-quality shirts. Just because you’ll feel a lot more comfortable splurging on a shirt, when you know you’re confident you’re picing a shirt that actually looks good on you, and you’ll actually love wearing.

      And even a tailored shirt that’s on the cheaper side will still look good enough.

      • DannyBlue says:

        Good point, I agree. Especially these days when many top designer brands offer very little added value in material (content & weave) and coloring of fabric over high-street brands – they generally do have a better fit initially, but as you said – same results can be achieved with after-market tailoring (adjustments) of cheaper shirts. So it’s a money saving technique with no real downside, as long as you have a good & affordable tailor/seamstress (for guys in traditional or rural areas – ask your grandma for help, as the today’s ultramodern ‘slim fit’ is direct copy of early 1960’s style and she may still have her good ol’ sewing machine).

        One thing I wouldn’t save on is fabric content – if one can, one should generally definitely go for 100% cotton, not the dreadful iron-free mostly polyester we see everywhere now – price difference is not very big and certainly worth it. I do have a few linen, viscose and silk-blend shirts but those don’t nearly as much wear time as plain cotton ones.

        Also, it’s pretty wise that you suggest that the guys that are starting out save on shirts because they will need that savings for good & lasting shoes and pure wool blazers/sport jackets (not those cheap&cheerful 100% polyester portable saunas). I think you already hinted about this when you mentioned monthly budget for clothes, because $300 can buy an excellent fabric 100% wool navy blazer with a good fit.

        PS: you have a small typo at point 8., it’s not ‘If you pan on’ but if you ‘If you plan on’.

        Thanks for the advice and keep up the great work.

        • Robert says:

          Thank you for the great comment.

          I pretty much agree with everything.

          Especially about the part about fabric. Well said.

  • Alex says:

    How do we check if it fits our chest?

  • Lorenz | Indochino Review says:

    Sound advice! Of course, these days a great way of getting well fitting shirts is online MTM. Did you ever give it a try?

  • Gerard says:

    Great articles as always dude! I’ll be sure to keep this one in my pocket app to refer to in times of need. Thanks again!

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