Filling your closet with the essentials of a versatile shirt wardrobe can be a frustrating exercise in multitasking, and it can take years. Having a list of what you want for each category is critical so that when deals come up, you can stay focused on what you “need” instead of just jumping on every deal. Items that can be used in tons of different outfits make the return on investment higher, making the opportunity cost of buying it lower (see this post for more about how opportunity cost impacts my decision making in menswear).

However, going for maximum versatility can be boring. After all, while we all admire the starched-white-shirt-in-the-desk-drawer-of-Don-Draper lifestyle, that would be super boring. Pattern, texture, collar shape and seasonality are the four main areas where you can start to mix it up.

Solids and Patterns

Solid shirts are the most versatile shirts you can own. In the realm of classic menswear, where you want to be able to go with or without tie, there are only two colors: white and blue.

White is more formal, blue less so. Depending on what kind of work environment or lifestyle you lead will determine how many solid blue or solid white shirts you will need. For instance, I only have two white dress shirts – one with double cuffs, and one with barrel cuffs – because I wear them so infrequently. For most people, light blue is the king of versatility because you will almost never look wrong with a light blue shirt on, even with a dark suit and dark tie.

Next in versatility are vertical stripes. Small repeating patterns such as pencil stripes, university stripes, and Bengal stripes are the most versatile. Shirts that have a white ground with blue stripes are the best place to start (and are the easiest to find).

Texture

Some textures fit better in a more formal context than others. A good rule of thumb is that a smaller, denser weave is more formal than a looser, larger or coarser weave. For instance, a poplin or end-on-end will look better with a refined suit-and-tie look than will an Oxford cloth. As Derek of “Dieworkwear” says, poplins are boring. You sacrifice zero versatility but gain some measure of visual interest by going with something like an end-on-end for business shirts instead of poplin. Coarser weaves like Oxford and royal Oxford are more at home with odd jackets, and particularly so when you break out the tweeds. Which brings me to:

Seasonality

One of my joys is having distinct cold-weather and warm-weather clothing. I’m currently planning a trip to Scotland, and can’t wait to pull out my Donegal tweed jackets and flannel trousers to take on the trip. In shirting, so, too, can you diversify your wardrobe with seasonality. That said, when we’re talking about having a jacket on most of the time, the concept of a linen or linen-blend shirt making much of a difference in the summer heat is a bit of a stretch. I wear linen-cotton blends all year-round, as layering can warm them up in the winter (though I do not wear my heavier Oxford cloths in the summer). So when talking seasonally appropriate shirt fabrics, everything except those cloths at the fringes (pure linens or, say, peached cotton flannel) can be pretty much worn year-round, depending on how warm or cool you tend to naturally feel. 

Collar shape

If you want the most versatile collar shape, period, then just get all medium-spread collars and be done with it. They look great with a tie and without. Cutaways, button-downs, and point collars, however, is how you add back in variety. Generally, don’t go too extreme (such as huge 1970s point collars, David Beckham-esque cutaways or tiny, anemic button-downs), and you’re safe.

Button-downs are right at home with Oxford cloth (the ubiquitous, stylish and unequaled OCBD) and with a generous roll, give an insouciant feel that have enormous charm. Cutaways give a rakish vibe that generally look best on guys with a sharp jaw and slim figure (though, when worn open-collar, look great on almost anybody, in my opinion). And point collars (such as this beauty from Drake’s), are an overlooked-of-late collar style that give off a lived-in, almost working-class charm that works quite well when done right.

As you amass enough shirts to wear day-in and day-out, you can start to branch out to other interesting areas: denims and chambrays, awning stripes, linens and flannels, and of course, colors other than white and navy. But that’s a post for another time.