How a Dress Shirt Should Fit – Proper Styling Details for Men’s Shirts

Dress shirts today are not just the foundation of classic men’s wardrobe that protect your outer garments from your body but they’re also worn on their own and because of that, fit is even more important because having a lot of excess fabric around your waist just looks unattractive. Today we’ll discuss how a dress shirt should fit and also touch on slim fit, skinny fit, and classic fit, so next time you buy a shirt, you end up with something that fits you really well, it’s more comfortable, and makes you look the part!

What Do We Mean By Fit?

Retailers often mean the cut of a particular shirt and they call something slim fit but we talk about how it actually fits on your body. In my experience, finding the right fit is so much more complex than just choosing the slim fit, skinny fit, or classic fit in your dress shirt. Why? Because we’re all humans, we’re different, we’re asymmetrical, and one simple fit doesn’t mean it fits you in the sleeve or in the chest just because it’s slim enough in the waist.

Unlike many other garments such as your waistcoat, your pants, your jacket, it is essential to get the shirt fit right from the get-go because there’s much less room for alterations. Alterations in dress shirts are not just pricey compared to the upfront cost but apart from adding darts in the back, they’re also visible which is unattractive.

Why, you might wonder? First of all, there’s no fabric reserve in the seams unlike with a pair of pants or a jacket and all the seams are exposed. An alterations tailor will likely not have the same thread and it’ll be difficult to replicate the exact stitch density and look of the original shirt. For example, your sleeve has to be shortened, because it can’t be lengthened, you would still see the different stitching on the cuff compared to the rest of the shirt and it just looks odd.

With that being said, if you have fit challenges because your body is very asymmetrical or you maybe have one arm that’s considerably longer and the other one, a made-to-measure shirt or a true bespoke shirt or custom shirt is probably the way to go for you to achieve a perfect fit. Fortunately, customized shirts are much less expensive now than they were in the early 2000s. There are online MTM companies starting at $40 a shirt so even if you don’t have a big budget, you can still get a shirt where the fit is customized to your body.

So, How Exactly Should A Dress Shirt Fit?

You should be able to pull a little bit in your armhole and when you reach forward, you should have ample room to move freely

You should be able to pull a little bit in your armhole and when you reach forward, you should have ample room to move freely

The Armholes

First, let’s talk about the armholes of a shirt which is a factor that is often neglected. Ideally, you want them to be as small as possible without restricting you when you move your arms. You should be able to pull a little bit in your armhole, there should be a little bit of room so when you reach forward, there is really no restriction and you can just move freely.

But why is this important? Well, if your armholes are too big, every time you lift your arms, you will pull out shirt fabric around your waist and it either comes untucked or you just have puddling fabric. If you have a jacket, that may not be so obvious but once you take your jacket off, there’s puddling fabric around your waistband which just looks awful. Well, I could just use sock suspenders, you might say, and yes, you’re right, but it’s just another element in your wardrobe, it’s uncomfortable and if you just get the fit of your armholes right, you don’t really have to deal with it in an everyday scenario.

Ideal Yoke and Chest Width

Ideal Yoke and Chest Width

The Yoke and Chest Width

The yoke is measured in the back, it’s the horizontal seam from one shoulder bone to the other. Ideally, that seam should extend just past that shoulder bone so you have enough range of movement but also, not too much excess. It is essential to have enough chest width so you can move comfortably just like with low armholes. If it’s too tight, you will feel it when you reach forward and it’s just uncomfortable and you have to think about your shirt when you should just not notice that your shirt’s there at all.

It’s particularly important to have enough fabric in your shoulder blade area, especially if your back is a little bit rounded, just like I am, otherwise, you’ll feel it and it’s difficult to move and reach forward.

The Sleeves

These days, shirt sleeves are often cut very slim which might look attractive when you just stand but as soon as you move up with your arm forward, you can feel a restriction or tension in your biceps area. To prevent that, you need more room in your upper sleeve despite having a smaller armhole and then ideally, the sleeve tapers further down because you don’t want an excess fabric in the area around your lower arm. Obviously, it all depends on the size of your biceps so if you have big biceps, you might have to go custom because you rarely find shirts that have a big upper sleeve but a very trim lower arm sleeve.

Correct Sleeve Length, Width and French Cuff

Correct Sleeve Length, Width and French Cuff

The perfect sleeve length for a dress shirt means that the cuff should end exactly at the base of the thumb. That’s easier said than done because when you stand, it’s really simple to achieve that but as soon as you move, you’ll need more fabric on the outside which typically pulls up your shirt sleeves. That’s why you want a little bit of a reserve but if you have a longer sleeve and your cuff is too wide, the shirt wrist comes all the way down to the beginning of your thumb or mid thumb and it just looks awkward.

Of course, you want your dress shirt to harmonize with your suit or your jacket and there are many different intricacies that are part of a well-fitting shirt and you can learn all about them in this video here.

Too much puddling fabric around the waist area

Too much puddling fabric around the waist area

The Shirt Length

A well-fitting dress shirt has the right length for you. In my experience, most dress shirts today are cut relatively short for me but I also have a long torso. Personally, I like shirts that are longer, that cover my bum, and that don’t have fabric on the sides. That way, I don’t have excess fabric inside my pants but I don’t have to worry about ever getting my shirt untucked in public. If you want to wear your shirt untucked, you want a plain hem that is the same length all the way around but frankly, it’s not really a dress shirt anymore if you wear it untucked.

Sven Raphael’s Ideal Dress Shirt Length

The Chest, Waist, And Seat

Most men have a different chest measurement than their waist measurement. Let’s say I am a 42-inch chest in a 36-inch waist. The six-inch difference is called the six-inch drop. In order to get that drop right, the shirt can either be cut from the get-go so it fits you perfectly but if you buy something off the rack, it is likely that it won’t be perfect. In that case, you can utilize darts in the back of your shirt that help you achieve the desired slimness in the waist without reducing the chest width.

As it’s not possible to make sure it’s larger because there’s no fabric reserve, it pays to get a shirt that has the right width and yoke and the right width in the chest and then if the waist is too wide, you can always reduce it.

For most men, the shirt has to be wider again in the hips that it wasn’t a waste. In my case, it’s extreme because I have an 8-inch drop from my chest to my waist and then a 30-inch increase from my waist to my bottoms. Because of that, most regular shirts will be tight in my seat and I can see that in the X wrinkles when I button the lower buttons of my shirt. It’s also uncomfortable and it feels restricting, so if you experience that, the only thing you can do is leave the bottom buttons undone and hope that they are covered by your pants. It may help to have a higher-waisted pair of pants if you have to do that or you go with a custom or customized shirt that allows for these extreme differences between your chest, your waist, and your seat.

collars that are too big, it creates unsightly creases

collars that are too big, it creates unsightly creases

The Collar

A collar that is loose and shows excess space around your neck looks sloppy and like someone who just got a shirt from their bigger brother. And if it’s so tight that your skin hangs over your collar, you look a bit like a pressed sausage.

So how do you know your collar is too tight or too loose? Well, the general rule of thumb is that you just have to be able to add two fingers in on the side of your shirt comfortably. The problem I have with that rule is that I can put two fingers in no matter if I wear a shirt that is two sizes too small or two sizes too big simply because my neck is flexible. Because of that, this rule is totally useless in my mind.

Measure the collar before deciding to purchase a dress shirt

Measure Your Neck

So, what should you do instead? I suggest you actually measure your neck with a measuring tape. In my case, I measure about 39.5 centimeters which is about 15.5 or 15.6 inches. Because of that, a shirt that is slightly larger about 40 centimeters or 15.5 inches are ideal for me. Once you’ve measured your accurate neck size, you can’t just rely on the collar size numbers that are provided by manufacturers because they can be wildly different. I’ve seen shirts that were marked as 15.5 inches but that were, in fact, 16.5 inches. Typically, the actual size is always larger.

Once you’ve measured your neck, I suggest that you measure the actual collar. To do that, you unbutton the shirt and you measure the inside of the collar. You measure from the button shank where it’s sewn on the collar to the end of the buttonhole when it’s laid flat. That gives you the exact measurement that you will have when you actually wear and button this shirt and believe me, chances are even if you have one size of shirt through different manufacturers and sometimes even of the same manufacturer, those measurements will be different.

So what does it mean for you when you buy a shirt? Bring a measuring tape and measure that collar and don’t just believe in what the brand tells you. Of course, once you go into high-end bespoke shirt making, people won’t just consider the shape of the collar but also the height and the typical fit of it. For example, my right shoulder is more sloped than my left one so if you have a symmetrical collar on your shirt, the tip on the right side will be further down than on the left. A bespoke shirtmaker can adjust for that in the height of the collar and the cut of the shirt so when you look at people from the front, the collar tips are in one level plane. Typically, this attention to detail is not something you will find in a made to measure shirt but only with true, dedicated custom shirt makers.

too tight dress shirt


Well, all humans are asymmetrical but all off-the-rack shirts are symmetrical and because of that, you will see flaws in the way a shirt fits. How can you tell? Usually, in forms of wrinkles.

For example, I mentioned my right shoulder is lower than my left one. You can typically see that in the back because you see a kind of quarter-circle wrinkle underneath my shoulder blade, you might see a wrinkle on the front side of my shirt, and you’ll see a wrinkle underneath my armpit.

On the other hand, if a shirt is too tight in certain areas, you’ll typically see X wrinkles or pulling wrinkles. If there’s too much fabric, you’ll just see puddling areas of fabric. If you have a round back and your posture is not the best, you also may see more wrinkles on the front side of the shirt around your collarbone. Now that you understand your body and you know where it’s asymmetrical, you can pay attention to those areas when you’re trying on new shirts off the rack.

Not all shirts are cut alike and the patterns are different and some will fit you better than others. However, in order to achieve a truly great fit, you will have to go custom because you are an asymmetrical person. Unfortunately, that can be rather expensive so for many men, a made to measure option, sometimes, online made to measure is a good middle ground between finding a shirt that fits reasonably well that is comfortable but also, affordable.

What About the Types of Fit?

If you go out and buy shirts off the rack, typically, you’ll encounter different fits. Right now, the most popular is probably the so-called slim fit which again, is just a kind of cut of a shirt. Other cuts include the classic fit, the modern fit, as well as the skinny fit.

FIT- classic fit (Source:Brooks Brothers)

FIT- classic fit (Source:Brooks Brothers)

The Classic Fit

The classic fit has a traditional silhouette, it’s very roomy, it often has big sleeves, big armholes, and enough fabric around your chest, waist, and seat. In the past, the classic fit was popular for two reasons; on the one hand, it was advantageous for manufacturers because it meant that one shape of a body would accommodate all kinds of people no matter if they were slim, medium, or big and on the other hand, the dress shirt was merely a form of undergarment that was not really seen on its own and so it didn’t matter if it was trimly fitting, neatly fitting, or puddly.

FIT - slim fit (Source:Brooks Brothers)

FIT – slim fit (Source:Brooks Brothers)

The Slim Fit

As it became more popular to wear shirts on their own right, people paid more attention to fit and especially in the last 10 years, the slim fit shirt has somewhat become the new normal. While a well-cut slim feature is not necessarily uncomfortable, most slim fit shirts are, in my experience.

Typically, the sleeves are so slim, especially in the upper sleeve that you always feel the restriction on your biceps when you move forward but I typically have higher cut armholes compared to the classic fit which is a plus if your sleeves are usually so tight that having excess fabric makes them look awkward so if you move forward, the sleeves typically pull back quite a bit which means you don’t have the proper sleeve length.

Slim fit shirts have darts in the back to provide a trim silhouette but that’s not always advantageous for people who have a bit of a belly or not super slim because otherwise, the placket will maybe gap and show X wrinkles. If you go with a custom shirt, you can have the fabric in the back extended so even if you pop up your shirt or you move, it will never show your exposed skin underneath of it.

FIT - modern fit (Source:Brooks Brothers)

FIT – modern fit (Source:Brooks Brothers)

The Modern Fit

Because the slim fit doesn’t work for a lot of men, the new modern or contemporary fit has been introduced which is somewhat in between a classic fit and a slim fit and therefore, combining the best of both worlds. You typically get a higher armhole, you get a little more room in the sleeve, get a little more room in your chest and your waist but it’s not excessive so it still looks like a well-fitting shirt without being uncomfortable or restrictive.

If you have to buy a shirt off the rack, this is my preferred fit but of course, it depends on the brand you buy it from but typically, if brands offer different fits, I like the middle one between slim and classic.

The Skinny Fit

Last but not least, let’s talk about the skinny fit which is popular, especially with younger men because they prefer a really trim silhouette of let’s say, a SuitSupply suit or just a very modern short jacket with a high buttoning point and because of that, they also want a very trim fitting tight shirt.

In my opinion, skin-tight shirts are not flattering for anyone but of course, it’s in the eye of the beholder and if you think it’s a good look, go for it. At the same time, if you’re interested in classic men’s style and you want to be able to have your weight fluctuate ever so slightly, this is not the fit for you.


Without a doubt, the best fitting shirt will always be the one that is made for you by a custom shirt maker with experience who creates a pattern from scratch just for your body. However, if that’s not within your budget and it isn’t for most men, you can still find plenty of options today that range from online made-to-measure to local stores that offer made-to-measure and even within that bracket, you find different prices. It can start at $40 and go all the way up to $250 or $300 per shirt. It mostly depends on the fabric and whether an interlining is used in the collar and if the shirt has a lot of hand sewing done or it’s machine sewn.

Older Post Newer Post