Specific sartorial rules govern how a dress shirt should fit. Unlike other types of rules, you shouldn’t break these ones.

When it comes to fashion, I’m all for being open-minded. However, I also think respect is of primary importance, and dress codes are one way we respect each other. As such, I believe every man should be able to answer the following questions: How do you tie a tie? How should you button a suit jacket? And importantly, how should a dress shirt fit? Today, we’re focusing on shirts.
Again, I’m not uptight. Casual clothing is a great platform for experimentation and joyful expression. But we’ll all have to wear a dress shirt properly at some point in our lives. And yes, this even applies to those of us with incredibly casual lifestyles. The dress shirt is the foundation of many outfits, from smart casual to very formal. Let’s explore it!
An Overview of Dress Shirt Fit

In general, a dress shirt should fit in a fairly body-con way while leaving room for comfortable movement. This typically means it tapers from your chest to your waist with no discernable excess fabric. It shouldn’t be skin-tight, but one should know more or less what your body looks like. The key is to ensure there are clean lines throughout. This is why many dress shirts feature those vertical folds on the back. It adds a soft structure to let the shirt’s body recede as it gets closer to where you’d tuck it in.
The chest, upper back, and underarms are close to your body but allow you to turn and raise your arms. Essentially, fit shirts allow you to fill them out as they follow the true lines of your silhouette. If it doesn’t do that, you can always bunch it up in the back if you’re wearing a suit jacket. Though ideally, you’d get it tailored.
This is a general overview with room for preferences. Of course, how it tapers depends on your body type, too. Dress shirts for bigger guys may need less taper through the waist, especially if you’re broad through your midsection. Additionally, mesomorphs with wide chests may also require less taper. Thin, rectangular body types or ectomorphs may need less taper.
How the Hem of a Shirt Should Fit

Many people overlook a proper hem fit. After all, you primarily wear your dress shirt tucked in. However, a proper dress shirt hem length is as important as other parts of a shirt. You want the front to fall midway past your pant zipper for a proper dress shirt length. This means that the back falls right at the middle of your seat. This allows you to tuck it in without risking it coming out even as you move. Yet, it doesn’t look like a dress when you wear it untucked.
Again, the overall key here is clean, close lines. You don’t want buttons to pull anywhere, and you don’t want your shirt bunching while tucked in your pants. Now, let’s get to more specifics with the question: How should a dress shirt collar fit?
How Should a Dress Shirt Collar Fit?

The collar is the most important part of the shirt. Even if the rest of your shirt is ill-fitting, you can always hide it with your suit jacket. However, your collar is always on full display, whether you’re wearing any type of tie or not. So, let’s say you’re in a pinch, and the department store doesn’t stock your perfectly fitted dress shirt. You should ensure the collar fits and figure out the rest later.
Fortunately, you only need to stick your fingers into your done-up collar. First, button it up. If you’re having trouble securing the collar, it’s likely too small. Even if you manage to get it buttoned, you may end up deeply uncomfortable the rest of the day.
Once you’ve done up the collar, stick two fingers into the collar. Use your middle finger and your index finger. You should be able to snugly but comfortably stick your fingers past your knuckles.
How Should Sleeves Fit on a Dress Shirt?

First, make sure you choose the right size arm holes. They aren’t as specifically sized as collars, as there’s a touch more grace room there. Typically, they’ll be small, medium, or large, with occasional XS and XL options.
You want to feel the armhole on your underarm but still be able to move without getting in your way. From there, the arm sleeve should taper as it approaches your wrist. When you button your shirt cuffs, you want them to fall at the base of your thumb above your wrist bones.
I prefer it a touch higher, and some prefer it just a bit lower. That’s okay. However, it should be able to peek out from under your suit jacket. And, it should never touch your initial thumb knuckles. And just so you’ll know how to talk to your tailor, ensure you know how to measure dress sleeve length.
How To Measure Dress Shirt Sleeve Length

If you need to measure your dress shirt length, you’ll need a soft tape measure. Measure from the nape of your neck all the way down to the thickest part of your hand. Make sure you start where you feel vertebrae and end just past the wrist bone. That’s your sleeve length.
Make sure you aren’t stiff and that you look straight ahead. Remember that you’re never fully standing at attention, so your sleeve length needs to reflect that. For a more in-depth explanation, see our comprehensive guide on measuring your sleeve length.
How Are Men’s Dress Shirts Sized: A Handy Dress Shirt Size Chart

Manufacturers size most men’s dress shirts using a combination of neck or collar measurements and sleeve lengths. For example, you may see a shirt size labeled as “16-34/35”. This means that the collar is 16”, and the sleeve length is between 34” and 35”.
Typically, the smallest collar size is 14”, and the biggest is 18”. Again, you don’t need your measuring tape as long as you have your fingers. However, it’s good to know so you can choose which shirts to try when shopping.
A size 14 is quite thin, though some grown men may be slightly thinner. Meanwhile, muscular men and generally broader men will fill out an 18. Most guys fall somewhere in the middle. The sizes are measured from button to buttonhole. To get the best, most accurate measure of a shirt, you’ll lay it down flat. Again, it’s too tight if your two fingers can’t squeeze in between the collar and your beck. If you can fit another finger in there, it’s too loose. You want the collar to be flush but comfortable.
If you’ve never understood the sizes of men’s dress shirts, check out the visual guide above. The guide even shows you how to correctly measure yourself for a dress shirt. Keep in mind that some brands also make XS shirts and even bigger ones than those in this guide. They aren’t that common because most people fall under the sizes in the guide. Even more, we’re all built differently proportion-wise. So often, you’ll choose the size closest to your proportions and then get it tailored.
How To Measure for a Dress Shirt
Here are the key lengths to get when measuring for a dress shirt. When you’re getting this specific, though, typically, a tailor will take care of this. It’s still good to know. You want to measure your shoulders via your back, from one shoulder to the other.
You should measure your chest, waist, and hips all around. If you can’t find off-the-rack pieces that accommodate your shape, go bigger rather than smaller. It’s easier to take shirts in.
I mentioned that to get your sleeve length, you’ll start at the nape of your neck. However, for the shirt itself, you also want the length of the actual cloth that makes the sleeve. This is the length of your shoulder to the end of the cuff.
Then, of course, you want the length of the top of your inner shoulder to be just past the hip. This is how long your shirt will be. Again, go longer rather than shorter if you can’t find the perfect fit.
FAQs on Proper Dress Shirt Fit
Getting the ideal fit on a dress shirt can be complicated. If you have more questions, we have you covered. Here are a few of the most common questions regarding men’s dress shirt fit.
How To Tell if a Men’s Dress Shirt Fits?
Your dress shirt fits if it tapers to your body, with the fabric lying flat and smooth. You should have a comfortable fit with a little room that allows you to move freely. There should be no excess pulling across the back of your shirt. Additionally, the sleeve length shouldn’t be too short or long, and the buttons shouldn’t pull.
Are Dress Shirts Supposed To Be Baggy?
No, a dress shirt should not be baggy. Not only does a baggy dress shirt look unprofessional, but it also adds additional bulk to your frame.
How Snug Should a Dress Shirt Be?
A men’s dress shirt should fit close to the body but comfortably. The buttons should not pull, and your arms should move freely. If your shirt is too tight in the collar, too short in the sleeves, or the buttons pull, it’s too snug.
Conclusion: The Perfect Fit

When it comes to the question of how should a dress shirt fit, there isn’t a lot of wiggle room — the length of the sleeves and overall length aside. It’s a traditional shirt meant for you to wear it traditionally. However, when dress codes aren’t an issue, feel free to wear whatever fits you best.
Any questions? Comments? Let’s start a conversation below!