Jeans $99 NOW $69 Each!

Free US Shipping (for orders of 139+) Free Returns/Exchanges  

How Should a Dress Shirt Fit: Achieve a Fresh and Classy Look

How should a dress shirt fit? It can be difficult at times to make sure that you are looking your best in a professional environment. There are a lot of options available in the dress shirt arena, but not all of them are designed to make you look your best. 

Here's what you need to know about how a dress shirt should fit and how you can choose one that is sure to give you a fresh and classy look.

Why Does a Well-Fitted Dress Shirt Matter?

You may have to wear a dress shirt to work, but who said you have to work to make sure your shirt looks perfect? Shopping for a dress shirt that fits you well may not be the most fun activity for your off-time, but having dress shirts that fit you well is very important for your professional image. By not paying attention to how your shirt fits, you may give others the wrong impression that you are:

  • Unprofessional or indifferent about your job
  • Immature or unable to deal with concerns of everyday life
  • Insecure about your appearance or unwilling to make an effort

You could take the time to convince your fellow employees that their impression based on your clothing is inaccurate, but it might be easier to just go buy a dress shirt that fits you well. Achieving a fresh and classy look that will make a great impression on your colleagues and friends may not be as difficult as you think.

Choosing the Right Fit for You

Many men wear dress shirts that are a couple of sizes too big for them. Buying shirts large is a good way to ensure that they'll be comfortable, and may make it easier to get your shopping done. Unfortunately, it isn't a good way to make sure you're looking your best. 

If you take the time to choose the right fit for your dress shirt, you will be able to build many great outfits from that shirt for a long time to come. Rather than choosing a non-fitted shirt that is too big for you, consider how a quality dress shirt should fit you and carefully make a decision that offers a flattering look.


Strong shoulders can help you to seem more confident. A shirt that doesn’t fit you correctly in the shoulders tends to make it look like the shirt is too big for you. Without the right cut in the shoulders, shoulders are underemphasized, making you seem unsure. A shirt that is poorly cut in the shoulders will make the entire shirt seem too big.

The sleeve should attach to the body of the shirt right at the top of the shoulders with a solid shoulder seam. Cheaper men's dress shirts tend to be cut large so that they'll be able to fit a broader amount of people comfortably. If you want to look your best, you should choose a dress shirt that hangs correctly at the shoulders. You'll know that the shoulder fit is too small if the seam between where the upper arm meets the shoulder is riding up closer towards the neck.


You can measure a dress shirt collar size by laying a dress shirt down flat and using a ruler to measure in inches from buttonhole to button. Most shirts fall between 14 and 18 inches. When you button the collar fully, you should be able to fit two fingers in between your neck and the collar of the shirt. 

Collar fit and size are only really important if you are going to be wearing your dress shirt with a tie or buttoning the top button. Most of the time if you'll be wearing the dress shirt in a professional context, like with a suit jacket or blazer, you'll want the ability to button it all the way up comfortably. 


You want your dress shirt to have a proper fit around the chest and provide some definition, but you definitely don't want it to be too tight to move your body comfortably or so tight that it conforms to your ribcage.

A good torso fit means that there is enough room under the armpit for you to move your arms freely. A well-fitted chest will also give you a complete range of motion when you flex your arms. It shouldn’t feel too tight on the back and there shouldn't be any pinching. 

You should be able to discern the chest under the shirt so that it appears that the shirt is filled out, but it should not conform to the lines of your chest. A good rule of thumb is that if you're standing still with your arms down and there's any pull in the buttons, the shirt may be too tight in the chest.


Just like shoulders, armholes are often cut larger in cheaper dress shirts in order to accommodate as many people’s body types as possible. However, there should not be fabric hanging under your arm. The armhole should be loose enough to give you a comfortable range of motion but tight enough that it is contoured to the lines of your arm and doesn't hang loosely. 

A good fit in the armhole will translate to how the shirt sits across the chest and back as well. If the armholes are too small they’ll keep your arms from moving freely and you'll notice tightening in the chest and back as well. When the armholes are too loose, there may be little motion in the shirt across the chest and back. 

Sleeve lengths should taper to follow your arms without lots of fabric hanging from your arm when held out straight in front of you. When you button the shirt cuff, the end of the sleeve should fall at the base of the thumb, although there is a little bit of wiggle room depending on what sleeve fit you want. In general, sleeve cuffs should never hang below your arm, but they should also be loose enough that you have a free range of motion. You don't want your shirt sleeves to be too short, and the perfect fit for shirt sleeve length goes right to your wrist bone. 


Dress shirts ought to taper from the chest all the way down to the waist. The shape of your body should be emphasized, but the shirt should still fit loosely enough for you to move around freely, and it should not be tight against the contours of your body. 

You should be able to twist your body around without feeling any tension in the shirt. A shirt should hang long enough that it can easily stay tucked in, but not so long that there is lots of excess fabric. 

A shirt that is untucked and unbuttoned should have a tail that falls just past the back pocket of your pants. When the shirt is buttoned and tucked in, you should be able to raise your arms over your head without your shirt coming out of your pants. 

How Performance Dress Shirts Can Help

Performance dress shirts are designed to give you an excellent fit while also providing great comfort. If you've been worried about moving to a more fitted dress shirt because you don't want to feel like it is restricting your movement, you will love the athletic feel of a high-quality performance dress shirt.

A great shirt like those offered by Twillory gives you a dynamic 4-way stretch that is undetectable in the hang of the shirt, but allows you a greather range of movement without feeling restrictions in the chest or back. Furthermore, these shirts resist wrinkling. You can save time in your morning routine since you don't need to iron them before you go to work, and ensuring you'll look your best throughout the day.

Why Untuckable Might Be a Good Choice for You

In order for your dress shirt to look its best, you'll usually decide to tuck it in when you're in a formal setting. However, there are many times when you might want the good looks of a dress shirt and a touch of formality, but don't want to go so far as tucking your shirt in. 

Untuckable shirts look perfect when worn with jeans and tennis shoes. These are the perfect shirts to give you a fresh, classy look when you want to get some drinks or go on a date. Untuckable shirts are cut to the right length to look great when worn outside of your pants. The shirts offered by Twillory are made of a cotton-spandex blend that helps the shirt to move with you and gives you excellent comfort while ensuring that the shirt lies perfectly. 

Perfect Your Style with a High-Quality Shirt

To give yourself the best chances of finding a comfortable dress shirt that makes you look great, it is best to choose a dress shirt from a high-quality maker. Lower quality shirts tend to have oversized armholes and baggy sleeves and will not have the details that give a shirt class. 

How should a dress shirt fit? A high-quality,affordable dress shirt like those offered by Twillory will give you the fit you deserve. Whether you are looking for a casual, classy option like an untuckable dress shirt, a performance dress shirt that will fit you well without wrinkling, or a classic cotton shirt with non-iron technology, Twillory is certain to have a dress shirt that you’ll love.