Everything you need to know about Dress Shirts



A primer on dress shirts.

In a hurry? Skip straight to my collection of dress shirts.

There comes a time in every man’s life when he puts away his tee-shirts, adorned with obscure gaming references, and dresses like a man. Usually this happens after college, but style knows no age my friend. Stuff your tees in a bag, and put away your polos. It’s time to grow up.

Dress shirts used to be the only shirts men wore. Take a look at mug shots from the 20s and 30s, and you will see men from all walks of life, even from the poorest neighborhoods, wearing respectable clothing, such as this fellow below.


Over the years, mens’ shirts have evolved to the myriad we have today, and dress shirts are no longer appropriate for every situation. Still, even though you can get away with wearing tees and polos in most work environments, I encourage you to develop a style guide for yourself, and collect the appropriate wardrobe.

Dress shirts are your most versatile shirt, and can be used to dress up or dress down. When building your wardrobe, you need to purchase at least 7 well-fitting dress shirts for each season, so that you never wear the same shirt twice in a row.

Some men are afraid of wearing dress shirts because they don’t want to appear too formal. However, dress shirts come in so many different textures and styles that you can make a unique wardrobe for yourself of dress shirts that fit any social circumstance, ranging from work to leisure. It all depends on the fabrics, patterns, and accents you use when choosing of crafting shirts, which I will delve into here in a moment.

Instead of highlighting specific shirts, I want to cover a few basic principles that go into choosing the right dress shirt, and then I’ll show you where to get them.

Anatomy of a Dress Shirt


The greatest error men make with dress shirts is buying shirts that don’t fit. This is because men go to malls and big brand stores, buying whatever shirt they find on a rack. These shirts are mass-produced to fit the greatest range of mens’ sizes. The problem is that every man is different, and most men look rumpled and unkempt when wearing shirts bought off the rack. You need a tailor.

Tailors are expensive. Luckily, you can now purchase shirts made-to-order online. If you take care to make good measurements of yourself, these shirts are guaranteed to fit, needing minimal alterations. I’ll get to shirt sizing tips in a moment, but for now, learn this principle: your shirt must fit.

The online tailor I use is Tailor4Less. I wrote the guide below based on their online shirt making wizard. You can customize any facet of your shirt and ensure that it comes in your size. This is the only way to get a good fit. Buying pre-made shirts is just guessing.

Make Your Shirt at Tailor4Less

There are three fits for shirts–slim, normal, and loose.


Slim Fit

The slim fit is in style these days, however, I urge you never to buy or wear slim fit shirts. Most men do not look good in them. Most men have a little extra baggage around their midsection. Slim-fit shirts make most men look fat, when normal fit shirts do not. The only men who can get away with slim fit shirts are skinny men.

Additionally, slim-fit shirts are often form-fitting, which is a feminine style. I encourage men not to buy clothing that shows off their physique, or shows off the contours of their bodies, as this is not classy. Timeless men’s style is humble, restrained, and not provocative.


Image source: Tailor4Less

Loose Fit

Loose fit is also an inappropriate style choice, though sometimes it is a necessity. Many men have never worn normal fit clothing their entire lives, because most malls sell loose-fit clothes to fit chubby men. While some big and tall men (like myself) may be forced to wear loose fit shirts, you can always avoid buying loose fit shirts by taking precise measurements of your body, and getting normal fit shirts tailored to your own body type. Loose fit shirts leave a lot of fabric hanging off your body, which makes it easy to move, but it looks frumpy and ugly.


Normal Fit

This is the fit I recommend for most men. Normal fit does not hug your body, making it easy to move in. It also does not hang off your body or blow in the wind. It looks custom tailored for you, and is much more attractive. Always choose a normal fit.


There are two types of sleeves–long and short. Never, under any circumstances, buy a short-sleeved dress shirt for daily wear. In a business or dressed-up setting, long-sleeved shirts always look better. If you ever need a shorter sleeved shirt, you can always roll up your sleeves, which is its own style statement. Additionally, you can use shirt sleeve garters to keep the cuffs of your long-sleeved shirt away from your wrists while working, which have a long history of use in banks and other white-collar working jobs.

Short sleeve shirts are for sports and athletic activities. When not doing those things, wear long sleeves.


Dress shirts have a rich history of collar shapes and styles, going as far back as ruffs used in the Elizabethan period.


Today, there is an established collection of collar styles that are acceptable in different circumstances.

Hard collar linings are found in business dress shirts. These collars are neat and look sharp. Soft collars have no starch in them, and are suitable for sport shirts (worn on weekends or in leisurely, casual situations).


Kent Collar

This is your standard dress shirt collar. It looks good on most men, and is never out-of-place. Use the Kent collar if you are unsure what face type you have, of if you want a collar that works in most situations.



Long Collar

The long collar is an exaggerated version of the Kent collar. Use this collar if you have a long face with a pointed chin.



Cut-away Collar

The cut-away collar or “spread” collar is a modern, youthful, and classy collar type. These look best on square-jawed men–think Frank Sinatra. They also look good on men who are wearing a tie with a large knot, or for men who choose to not wear a tie and leave the top shirt button unbuttoned.


Button-down Collar

The button-down collar is a casual one. Use this for sport shirts with soft collar backs. The rule of button-down collars is to always keep them buttoned. These collars look ugly when unbuttoned, especially with soft collars.

Protip: If you want to use a collar pin, buy a shirt with a hard, button-down collar, and remove the buttons. Then, you can place the bar or pin through the eyelets, instead of having to pierce your collar.



Round Collar

The round collar is an archaic collar style that is rarely seen these days. It looks best on men with round faces–think Winston Churchill. Men with round faces can get away with wearing the Kent or cut-away collars, but round collars look particularly good on them. Because the collar is so rare, it may be seen as too formal by some, so make sure to use it on youthful, colorful shirts along with a youthful blazer.




Wing Collar

This is a formal collar type. It is only suitable with a tuxedo. Choose this collar only if you are wearing it with a black tuxedo. You cannot wear ties with them–you must wear bow ties.




Straight Collar

The straight collar, also known as the Chinese collar, is historically unconventional, but has become popular of late. Use this collar if you are trying to perfect a rigid, uniformed look. It is formal and business-like, not casual. You do not wear a tie with the straight collar.


Tab Collar

The tab collar mimics the appearance of using a collar bar, without the need of one. It includes a small strip of fabric connecting both collars, that is designed to fit behind a tie. The tab collar is a good choice for men who want a snug, uniformed look while wearing a tie, without having to fuss with a collar pin. This style should only be worn with ties.


With a well tailored blazer or suit coat, shirt cuffs stick out and are an opportunity for a man to show a bit of breeding. There are a number of ways to do cuffs–from straight cuffs (more traditional) to cut cuffs (modern, youthful). Here are a few cuff guidelines when choosing cuffs.


One button cuffs

These are your standard shirt cuffs. They look good on both dress shirts and more casual sport shirts. They look best on men with normal or long arms.


Two button cuffs

These cuffs are unconventional and exaggerated. They look best on short men who want to create the illusion of longer arms. Note that you’ll likely have to have the sleeves of your jacket shortened to show the complete cuff.


French cuffs

These are the most formal and most traditional cuff type. It used to be that all shirts had french cuffs, but nowadays, only formal shirts have french cuffs. French cuffs give you the opportunity to wear cufflinks, which are a nice, subtle way of adding character to your every-day look. I suggest that men choose french cuffs only for their most formal occasions–church, the symphony, and so on. Some men can get away with wearing french cuffs for everyday use, but these men typically wear suits on a daily basis, and have a wide range of ties and cufflinks to experiment with.


Double cuffs

Double cuffs are twice as thick as normal cuffs. They look formal, and are really only suited for tuxedo shirts. Personally, I find that double cuffs snag on my blazer and are distracting.

Chest Pockets

Chest pockets are suitable for sport shirts. They turn any dress shirt into a more casual shirt. If you want to pull a casual sportsman look, then soft, button down collars with chest pockets are the thing for you. If you choose not to wear a blazer with your shirt, then you may want to add a chest pocket to it–however, I suggest you always wear a blazer with your dress shirt, and keep your pockets on the blazer, not your shirt.

Your pockets should not have flaps. Pockets with flaps are good for outdoorsman shirts and activity shirts, not dress shirts. Also, you should never have more than one pocket per shirt. Two pockets are an extravagance. What on earth would you put into two shirt pockets?



The placket is the buttoned seam that goes down the front of the shirt. A seamless placket is sleek and looks good. I suggest a seamless placket for all dress shirts. A normal placket has a seam going town the left-side, giving the appearance of a strip of cloth down the middle of your shirt. These plackets appear more “heavy duty” to me, and are appropriate for sport shirts. A placket that hides your buttons is unconventional. While popular with young urbanites, I suggest you skip the placket that hides buttons. You don’t want people to think you’re wearing a tee-shirt, now do we?



The hem of your shirt is the very bottom of it. There are two types of hems–tail and square. Put tails on shirts designed to be tucked in. The excess fabric prevents the shirt from being untucked when bending over or reaching. It also gives you excess fabric to attach shirt stays to. Never leave a shirt with a tail untucked. This looks sloppy. Shirts with square hems are designed to be worn untucked. Today, many men wear shirts untucked. If this is you, buy a sport shirt with a squared hem.



Pleats are folds in the back of the fabric designed to give way when you bend or stretch. They are typically found on store-bought shirts as a measure to ensure their shirts will fit anyone.

Since we are purchasing or making custom-fit shirts, there is no need for pleats. A shirt with no pleats will look better, make it easier to iron, and feel like the shirt was truly made for you.

There are two types of shirt pleats–box pleats and side folds. Box pleats are most common. If you must use pleats, I suggest using side fold pleats.



Traditionally, shirts have been made from cotton and linen. Today, most dress shirts are made from man-made fibers, which are essentially plastic. Now, there are certain benefits to using man-made fibers, but in my opinion, natural fibers make the shirt last longer, keep the colors from fading, and have a much more comfortable texture. I recommend shirts made from cotton and linen. Here is a breakdown of the different cloth types you will come across:



Cotton, made from the cotton plant, is my favorite shirt material. It is famed for being breathable, which means you won’t get too hot while wearing it. However, it is notorious for wrinkling up, which means you will be ironing your cotton shirts after every wash. Additionally, cotton tends to shrink. You can often get pre-shrunk cotton shirts, and I recommend you do when the opportunity arises. If your tailor or shirt-maker does not offer pre-shrunk cotton, call them and ask them how many sizes bigger you should buy your shirts to keep them at the right size after washing.



Linen, made from flax, is a light, breathable, and somewhat transparent fabric that is often used in summer shirts. I have two wardrobes–a wardrobe of cotton shirts for fall and winter, and a wardrobe of linen shirts for spring and summer. With linen shirts, you may need to wear a thin cotton undershirt so that people can’t see through it. This is especially important if you have a mighty mane of dark chest hair. (Ahem. Like me.)


Easy-iron shirts are mostly cotton, with a small addition of man-made fibers. These are…acceptable. Part of me is tempted to be a cotton purist, but honestly, ironing is a pain in the whatsit. A small percentage of man-made fibers in a cotton shirts still keeps it breathable, but also makes it easy to iron.


Wrinkle-free shirts are almost entirely made from man-made fibers. I HATE these shirts. They feel like plastic. I once rented a tuxedo for my brother’s wedding. The shirt they gave me was wrinkle-free, and it felt like I was wearing a garbage sack. You sweat in these shirts, because man-made fibers do not breathe.

Now, some 100% cotton shirts are also wrinkle-free. Tailors achieve this by soaking the fabric in a chemical that releases formaldehyde, as a recent New York Times article demonstrated. These shirts are fine–however, there are some reports that the chemical agitates sensitive skin. If you have sensitive skin, avoid wrinkle-free cotton. If you have hardy skin, make sure that any wrinkle-free fabric you buy is 100% cotton.

How to Build Your Wardrobe

It is hard, if not impossible, to have the artistic control you want with shirts you buy from shops. This includes boutiques like The Men’s Warehouse (which, incidentally, is notorious for charging high prices for low quality plastic stuff). Your only solution is to find a tailor.

I recommend Tailor4Less, which has an easy online shirt making wizard that will help you craft the perfect shirt in your size.

Make Your Shirt at Tailor4Less

Another solution is to purchase dress shirts from Paul Fredrick. While the don’t make shirts-to-order, they make quality shirts in a wide variety of sizes with the range of choices I need. They also have a huge big & tall selection–and trust me, it is damned difficult finding quality stuff for big & tall chaps. Plus, Paul Fredrick guarantees a perfect fit–meaning that if it doesn’t fit, they’ll ship you a new one that does or refund your money.

Shop dress shirts at Paul Frederick

Note on Sizing: Paul Frederick has their shirts organized by collar size and arm length. If you can’t find a shirt with both the perfect collar size and arm length, choose one with a perfect collar size and sleeves that are too long. You can always roll them up, get them taken in at an alterationist, or use shirt sleeve garters.

Here is a short video that explains how to get your neck and arm measurements:

Here are some links to useful sections of the site:

Here is a selection of dress shirts, handpicked by me, that adhere to our classy guidelines, mentioned above.

Dress / Office Shirts

Single button cuffs, 100% cotton.

Cut-away Collar

More colors and styles available. Click to browse more.

Kent Collar

Single button cuffs, 100% cotton. The Kent Collar is called the Long Collar on Paul Fredrick.

More colors and styles available. Click to browse more.

Activity / Outdoor / Casual / Weekend Shirts

Sport Shirts (button-down collar)

Single button cuffs, 100% cotton. Note: Even though these images depict these sport shirts with ties, it is proper style to not wear ties with button-down shirts–and to ALWAYS keep the collars buttoned down. If there are buttons, use them.

More colors and styles available. Click to browse more.

Formal / Church Shirts

100% cotton. These formal shirts have french cuffs and Kent collars. I couldn’t find any without chest pockets.

More colors and styles available. Click to browse more.

Big & Tall Dress / Office Shirts

These come in a maximum neck size of 20 inches, which should suit most men. For reference, I am a very large man in excess of 300 pounds, and I wear a 20 inch neck. I have short 32 inch arms, so I order a 35 inch arm and it ends up fitting just fine. Their 20/35 shirts fit me perfectly.

More colors and styles available. Click to browse more.

More Options

In an effort to make more money, shirt manufacturers have created an industry of embellishments for dress shirts, most of which are totally unnecessary. Let me break down a little style philosophy and explain why I disapprove of most of them.

Embroidery / Monograms


There is a famous scene in the BBC’s Jeeves and Wooster where Bertie comes home with a new pair of monogrammed gloves, thinking they are “quite smart”. Jeeves responds, with the customary wit, that they must be for men who are in a habit of forgetting their own initials.

Monograms violate our rules of style because they are too showy. Why does the world need to know what your initials are? Engraving your shirts with your own name gives the impression that you’re so proud of your fancy clothes that you want the world to know exactly who owns them. In effect, monograms are for insecure men subconsciously trying to raise their own self-worth by wearing fancy clothes.

Never let the shirt wear you, my friends. Instead, be a man who gives purpose and dignity to the shirt only when he puts it on. It is he that wears the shirt. The shirt attains dignity and style for being on him, not the other way around.

Different Collar Fabrics


It’s trendy nowadays to have different fabric colors for the collar, or for the inside of the collar.

Sometimes these are fairly restrained–a white collar with a striped shirt, for example. Sometimes these are outrageous–a pink checkered collar with a blue plaid shirt.

Most of the time, this experiment ends up looking ridiculous. Very rarely, men can pull off a collar and shirt fabric combination that works well. My advice is to not have a different fabric for your collar. If you must, only do it on the inside of the collar.

Different Cuff Fabrics


My opinion on different cuff fabrics is the same as for collar fabrics.

It is hard to pull off in a classy way, but if you do decide to do it, do only the inside of the cuff.

Elbow Patches


Elbow patches belong on sports jackets only–and even then, they must be a dark leather, preferably suede, or a patchwork cloth. Having patches on elbows of a dress shirt is just irresponsible.

A Note on Shirt Colors

Every man should have a plain white shirt in his wardrobe. It is versatile, and attractive. Blue is also a safe color, as most men look good in blue. The problem is that most men have figured this out, making blue the primary color for office shirts. I suggest you avoid solid blue shirts. Try for solid white shirts, and then colored striped or window-pane shirts. Sometimes, men can get away with darker colored shirts, but lighter colored shirts are safer.

Colored Button Hole Threads


Now this just makes me angry. Young hipsters walk around with a nice reserved eggshell-blue windowpane shirt, and then ruin it with bright red buttonhole threads. I mean, honestly. This is nearly as crass as a Kim Kardashian photo shoot.

Chest Pleats


Chest pleats are for white tuxedo shirts only. If you are building a shirt to wear with a tux when attending the opera, then fine. Otherwise, don’t be silly.

That’s That

This wasn’t a short read. I congratulate you on reaching the end! You now know all you need to craft an elegant, functional shirt with timeless style. Head on over to Paul Frederick to build your wardrobe.

Build Your Wardrobe Now

Brandon M. Dennis
Hello, fellow beardsmen! I'm an author, marketer, and story-teller. Read my swashbuckling fantasy sea adventure novel, The Tale of Cloran Hastings, and click my name to learn more about me. Enjoy the site!

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