Shirting: Your Responsibility


Dress shirts are a cornerstone of dressing well. If you are wearing a suit, you are wearing a dress shirt 95% of the time. Business casual still means a dress shirt in most places. On the weekend, dressing up to go out? Wearing a dress shirt.

I don’t expect most readers to be trying to curate their shirt collection down to thirty or organize them in the only logical manner of white-ROYGBIV-Black, but I think men should have dress shirts. Five shirts is a good starting place for most people.

You want one to be white, more likely two. They will go with anything and are a linchpin of any good wardrobe. Blue is another staple and basis for conservative dress attire. The last 2 may offer you a bit more flexibility. Make one of them a pinstriped shirt, or if you have the gumption go for butcher stripes. The last one is your wild card. Think about color and pick something that you like, or that your special ladyfriend thinks flatters you. Checks or tattersall are also good options for the wild card.

One of your two white shirts should be the best you can afford at the time you are starting. This should mean that you get to go to a reputable shoppe of some form where you can get measured! It makes buying the rest of them easier. Most guys get shirts that are too big. You don’t have to have them hewn to your skin like a wetsuit, but you want it to be closer to your body than you may be accustomed. Even if you are a larger gentleman, don’t fall for the trap of getting shirts that are too big. A blousy and diaphanous shirt will just make you look bigger no matter your real size. There is not much to tell you besides see if you can try the shirt on. There are a lot of possibilities out there. A lot of shirting lines now offer a slim or athletic fit that is not as big at the waist, though they often are still huge in the arms. You don’t want the shirt to bunch out of your pants and you don’t want it to fly away from our torso between your arm pit and your waist. I like to be able to tuck my shirt into my pants without having to bunch the material to make it fit. Your body frame is what it is, so don’t try to disguise it with your shirt.

Your neck should fit comfortably with two fingers able to slip between your neck and the shirt. That is it. If you can’t breathe, it is too tight. If you can see a gap between the collar and your neck just standing still, it is too loose.

The arm length is easier to figure out. You don’t want it to bunch up on your arm. While a decent tailor can shorten the sleeves for you, it is easier if you find the right length from the get go.

After I started writing this, Primer published this handy guide for how a shirt should fit. Generally, I agree with it. I prefer a slightly tighter fitting shirt with only 2-3” total on the waist in slack instead of 3-4”.

As far as material, look for cotton shirts. These are going to feel the best and they have great breathability. It does take some effort or money to keep them pressed, but it is better than the option. A small amount lycra will sometimes be used for stretchy shirts. They are best suited for thinner or athletic guys because it allows an even tighter fit. Gentlemen of more substance may not find this comfortable or as flattering as a well fitted cotton shirt. While it is tempting to get the “no-iron” or “wrinkle-free” shirts, they are rarely worth it. I may have a few of them, but they still need ironing to look crisp. Coupled with the formaldehyde used to reduce the wrinkling and you may not want them near your skin.

We’ve discussed a basic load out of shirts, colors, materials, and fit but we still need to define some terms for future discussions. Structurally, there are two defining qualities for a dress shirt – collar & cuffs.


The three basic kinds of collars are button-down, point, and spread. Point is the most common one you will find as well as the one you wear most of the time. It is the default setting for dress shirts, especially if they will be matched with a tie. Button down is just what is says – buttoned down. This less formal style of shirt is a good idea for dressing down the rest of your outfit or matching with something for a business casual event. Spread collars, and the more extreme cousin cut-away collars, have a large spread between the points of the collars. These are perceived as more formal. They are much more common across the pond in Jolly old England, and only recently got serious traction in the states.




If you are on the thinner side of things, be careful about the spread collars because the proportions will be a bit wonky. On the flip side, gentlemen with a more substantial build have to make sure that a button down shirt is sized correctly or you will have too small a neck which makes the button downs looks forced.

The wider the spread, the more formal the shirt. A button down shirt is the least formal or most casual of the dress shirt universe while the semi-spread has the most formal connotations.


Cuffs are generally going to be barrel, or buttoned, cuffs or french cuffs. The more buttons, the more formal. I am a fan of two buttons on the cuff just for some additional interest without it being over the top. French cuffs are wonderful and elegant. The problem is that you have to also have cuff links to go with them. You can use silk knots, but honestly, I have never quite clicked with those.

When you see two buttons horizontal on the cuff, it is because the shirt is made to fit multiple arm lengths. The tightness of the cuff will define where it falls on your arm.

French cuffs are the most formal of this example list. Conversely, the single button barrel cuff is the least formal or most casual.

Hopefully this will be a good primer for dress shirts. We’ll revist the topic to talk about cuff links, advanced shirting, and what is available around town later. For now, shirt up gents!