Wardrobe Basics: The Dress Shirt

Since men began to eschew suits and sport jackets over the past couple of decades, the dress shirt has become the first line of sartorial armor that he shows to the world. Every man has a dress shirt in his closet that makes him stand taller, that makes him ready to take on the world – funny for a garment having its origins as underwear. A rather uncomplicated piece of clothing, it has gone through many innovations and transformations to get to where it is today. Gone are the stiff, detachable collars, added in were buttons and pockets. It is now donned by many as proper business attire. It comes in a seemingly endless choice of dizzying patterns and colours, with an array of collars to suit any man’s style.

Typically made of cotton, from oxford cloth to Sea Island cotton and everything in between, it can also be made out of wool (or wool blend), linen and, even silk for those rare gents that dare to don it. It is the staple of menswear. A man will find that as he ages he has amassed a large collection of dress shirts without ever intending to do so. So the question to the man just starting out building a wardrobe is this: which types of dress shirts does one need when beginning to build a ‘grown up’ wardrobe? This question is trickier than one may think as there are many factors to ponder. One should consider his profession, his needs, his means, climate – and the list goes on and on.

Shirts can be had in the same ways as suits: off-the-rack, made-to-measure, and bespoke. As with the suits, we will be concentrating on the first to due to availability and cost.


Even if you are not a clotheshorse like myself, you should all have at least a couple of dress shirts in your wardrobe already. These will most likely be of the off-the-rack kind. Like with any piece of tailored menswear, the most important factor will be fit.

Torso and Waist: There are several different philosophies on fit in regards to how a shirt should fit around the torso and waist. The traditionalists state that a shirt should be roomier around the midsection, a so called ‘full cut’, while the current trend is towards shirts that are very form-fitting. It is really a preference. Just make sure it fits your body and your – you do not want it to look like you are wearing a burlap sack, nor do you want the buttons pulling because it is too tight.

Back: This is something to watch. I am not just including back here, but the armholes as well. With the advent of slimmer fitting shirts, many makers have raised their armholes significantly making for a restrictive fit if not the proper size/style. Basically, try on the shirt. As for whether you should get box pleats, side pleats, or no pleat at all will be dictated by your body. For larger men, a box pleat can help the shirt fit better without adding bulk. Side pleats are ideal as they are more functional, though not usually found on most off-the-rack shirts. For the slimmer gents, no pleats should be necessary.

Neck: This one is easy. The old adage still stands – you should be able to fit two fingers in between your collar and neck when buttoned. Better shirt makers mark their shirt with neck size – for example, I measure 15 ˝ inches. While you should always try it on, this neck size is usually pretty standard. Better retailers will measure both your neck and sleeve when you come in looking for shirts. Commit those numbers to memory and this will make purchasing shirts in the future a breeze.

Sleeve: As mentioned above, better shirt makers will also mark their sleeve length. The rule here is that the shirt should fall basically where the thumb and the wrist meet. Again, a better menswear store will be of great help here. Bring a good fitting odd jacket/blazer when you go shirt shopping. This will better highlight where the shirt sleeve should end. Ideally, with an odd jacket on a half inch of the cuff of your shirt should be showing – but no more.

Length: This is a big one. Most men when they were younger wore their shirts untucked (admit it; we all did it at one time of another). However, a dress shirt is not a t-shirt or sport shirt. It is for looking appropriate and put together, not casual and sloppy. This why men sometimes balk at the length of the tails on a shirt – they should be long. A properly fitted dress shirt should have the tails resting over your posterior. This ensures that when seated, your shirt does not come untucked.


As with suits, if all your measurements are taken properly and the shirt is made to those measurements, the shirt should fit like a dream. While it is recommended that should start off with off-the-rack to when building your wardrobe, made-to-measure has many benefits than just fit. Made-To-Measure shirts are an affordable luxury. How often in this modern world do you have something made for you? Made-To-Measure shirts are for your measurements and with fabrics, colours, collars, cuffs and details that are chosen by you. Most of my shirts over the past while have been made-to-measure for this reason. While my sizing is a bit on the unique side, my tastes have expanded and I want to try different things when it comes to men’s clothing. Made-To-Measure shirts are a great, comparatively inexpensive way to start experimenting with your own unique style.


There are literally dozens of collars types out there for you to choose from. If you are going the made-to-measure route, you will have many of them available to you. In the off-the-rack variety, the selection is a little more limited. For simplicity sake, we will look at the three most popular and most practical collars; the medium point (or regular), the button-down, and the spread.

Medium Point (Regular): This is the jack-of-all trade collar. It looks great with a tie, but can be worn without. It should be the starting collar in your wardrobe.

Button-Down: Our cousins south of the parallel absolutely embrace this collar. Donned by the Kennedy’s, Gianni Agnelli, and even Warren Buffett, it is part of their culture and their unique – a true American classic. It reeks of prep school and casual nonchalance. Think blazer, chinos and loafers. It looks great with a tie, but holds up even better without one (as the buttons keep the collar staying where it should).

Spread: Now a nod to the motherlands style: the spread collar. This collar type is quintessentially British. Envision this shirt worn with a silk tie with a hefty knot, a well-cut suit and a pair of wingtips. For a suit, but even with a more sophisticated jacket and trouser combo, the choice of a spread collar is unbeatable.

Whether you choose off-the-rack or made-to-measure, no matter what your collar choice, it is important to keep in mind when you are looking to build a wardrobe – a good rotation of shirts is essential. Starting off with a few whites and some basic colours such as blue are a great starting point and will give you many different options.

© Copyright 2021 - John McNabb Clothiers