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Making sense of men’s dress shirt sizes: How to get the perfect fit

Look great no matter what your dress code requires

mens sweater over dress shirt man with a cardigan
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Growing up, our understanding of sizing in our clothes was quite simple. We knew from experience whether or not we were a small, medium, large, extra large, or one of the big and tall sizes. The best casual shirts are always categorized in those sizes, making it easy for us to find the right size. However, there are further complications when you get into the shirt’s fit as there can be a wide range of categories from extra slim, slim, classic, modern, and even more cut types.

Once we get into the tailored wardrobes, dress shirts get a lot more complicated as they ditch the typical sizing categories and go with something different. Learning how to measure shirt size in the dress shirt world is vital to looking great. The sizing switches from letters to two vague numbers that make no sense if you are unaware of their purpose. We have the answer for you. Here is how to do it in a way that will have your dress shirts fitting great at all times.

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Measuring the neck

A man in a white button up dress shirt.
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When wearing a dress shirt, there is one place that is always noticed: the collar. It is the mouthpiece of the shirt. The collar is cut in a way that, when combined with the tie knot, it forms an arrow starting from your waist and pointing up towards your face. This, of course, is meant to keep the focus on you and what you can do. Since the place where the collar and tie come together is the most noticeable and significant place on the shirt, it is essential that it fits properly. If it is too loose, it hangs open and looks sloppy. If it is too tight, it can make your face look like it is ten pounds heavier. Getting the right fit is simple.

The first number in the two-number sizing is the circumference of the neck. Using a measuring tape (sometimes labeled as a body measuring tape or a tailoring ruler), hold it at the front of the neck just below the Adam’s apple. With two fingers on the inside of the tape, wrap it around your neck and make it snug (not tight) against the skin. The two ends should come to meet over the fingers at the front of the neck. Mark with a finger and note the number. Most guys will be between 15 inches and 18 inches.

Measuring the sleeve

Man in tux with ring and watch
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The second number on a dress shirt’s size tag is the arm length. Getting the arms right is also vital to making sure your shirt fits you correctly. When you wear a dress shirt, the cuff of the sleeve is designed to sit on the wrist bone, where the radial bone meets the hand (cheers for high school anatomy!). If the shirt is too short, it disappears under the suit, and you lose a bit of depth in the look. If you’re not wearing a suit, then the shirt looks too small, and you are forced to roll the sleeves at all times. If the shirt is too big, it will show too much beneath the suit sleeve, making you look like the jacket is too small. You can’t even lose the coat to fix the problem, as the long sleeves will make the shirt look like you borrowed from your older brother. Getting this correct properly fixes all these problems.

Take the tailor’s tape and lace it at the base of your neck, on the spine where the neck and back meet (it is best to get help with this part of the process). While holding that end in place, slide the other hand to the shoulder bone and hold it in place there. Keep the tape in place at the shoulder bone and swap the hand you are holding it with so you can slide the lead hand to the elbow and repeat the process. Finally, mark the end at the wrist bone. Most men will be between 32 and 38 inches. Remember that even if you get this perfectly right, your suit should be tailored in a way that there is 3/4 an inch visible under the sleeve.

Getting the right cut

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Hassan OUAJBIR / Pexels

Finally, getting the fit of the shirt correct is vital as well. Of course, there are all kinds of fits on the market, from extra slim to executive fit; the torso of the shirt has to fit your body in a flattering way, or the top two measurements don’t matter. If you are a smaller size above, like a 14/33, then you will likely find a lot of slim-fit shirts since the industry essentially assumes more petite men like that are trim in the body area. If you are on the opposite side of the spectrum at an 18.5/38, you will have a more challenging time finding a slim-fit shirt because men with that kind of measurement don’t often see the rest of their torsos slim. That doesn’t mean you should resign from wearing improperly fitted shirts; look for the proper cut. And if you can’t find one, custom dress shirts are more and more affordable by the day.

Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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