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5 Tips To Know if Your Dress Shirt Fits Properly

Cropped man buttoning his white dress shirt.
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As offices are starting to slowly open up again and weddings are being rebooked, you can’t help but think about the major wardrobe shift that is about to happen. The sweats you’ve been wearing on repeat over the last few months have probably seen better days. Many people are treating coming out of quarantine with a “new year, new me” mindset and so a wardrobe upgrade is a great place to start on your self-improvement journey.

Even if you’re not into fashion, every man’s closet should include a basic dress shirt. With closet staples like this one, it’s always important to choose quality over quantity here, as it is something that will never go out of style. Just like your “fancy” sweats during quarantine, you’ll want to wear this on repeat for the many rescheduled special occasions coming up.

When choosing a dress shirt, the fit is by far the most important aspect to consider. While it’s the unsung hero of any suit look, you’ll also wear it on its own a lot, which make proper measurements even more important. Ahead, we offer a guide to choosing a dress shirt that will surely fit on you.


You might think paying attention to the collar is silly. Anyone who has worn an ill-fitting collar will tell you that this can easily ruin your day. If it’s too tight, you’ll feel extremely constricted and if it’s too loose, it will look sloppy. The sweet spot is when you can place two fingers between the collar and your neck without feeling any discomfort. If you can fit more than a couple fingers here, that’s a sign that the collar is too loose. Remember, the collar is a focal point when talking to people and in pictures, so this small detail is actually far more important than you think.


So, you’re at the mall in the men’s dress shirt section and you see slim, skinny, and classic fit. How do you know which one is right for you? These different fits are created for body type variations and trends. A slimmer fit shirt is a more modern approach to dressing, while the classic fit is roomier and for comfort.

We recommend going for a slim fit shirt, whatever that means for your body type. To test out if the body of the shirt is right for you, button it all the way and tuck it in. Once you’re here, look in the mirror. The buttons should not be pulling across your chest or rib cage, not even a little. Remember, when you sit down, they will pull even more, so you’ll want to leave a little room to grow here. If the shirt is too big, you will see excess fabric building up around the sides of your waist. Even if your priority is comfort over style, the bustling of fabric looks costume-like and sloppy so do not overlook this, even if its purpose is to be worn under a suit jacket.

Man buttoning his dress shirt in the living room.


This very minor detail affects how the rest of the shirt hugs your body so it’s crucial to note. If the shoulder seam is positioned up on your shoulders, your arms won’t be able to move freely, and you’ll risk tearing the fabric. If the shoulder seam falls below the shoulder towards the arm, you’ll be swimming in excess fabric and need to size down. The golden rule here is for the seam to gently kiss where your actual shoulder ends.


The rules concerning sleeves follow suit (pun intended) to those of the body. You do not want to see any pulling fabric along the arms and excess fabric building up. The true sleeve test is to move your arms up, down and side to side. If you feel any tight rubber-band sensation on the elbow or wrist, you need to size up or choose a different fit. Equally, you absolutely do not want to see any fabric folding over the cuff on your wrist. This means you need to size down and probably go for a slimmer fit. The cuffs should allow enough room for you to take the shirt on and off without having to unbutton them.


A dress shirt should always be comfortably tucked in, but in order to test if it’s the right length for you, untuck it and look in the mirror. It should fall two to three inches below the belt line. The next fit test requires you to tuck it in as you would in a normal day. Once tucked, raise your arms up to the sky. Did the shirt pop out? If yes, then this length is too short for you. When a shirt is too long, the discomfort in your pants is real. This can be fixed with tailoring.

We recommend going to a tailor to make sure your top falls precisely below the belt line or a half inch below a blazer.

Man putting on his dress shirt in front of a window.
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Made to Measure

If you’re still struggling to find a dress fit that you look and feel comfortable in, a made-to-measure or a bespoke custom shirt is probably for you. Many men actually have asymmetrical bodies where one shoulder hangs lower. In this case, it will be difficult to pass all of the above fit tests. Although a little more expensive, the garment is literally being tailored to flatter and fit your body in the most customizable way. Thinking about that will justify the cost. Indochino is a great accessible made-to-measure brand with showrooms across the country. The brand even offers instructions on how to have a virtual fitting right from home.

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