Building a Versatile Shirt Wardrobe

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).


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:


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.


Shopping Rome: Jaja Camiceria

Giuseppe Rossi of Jaja Camiceria. Nice shirt.


By serendipity, I found Jaja Camiceria while walking around Rome one day trying to find a good lunch. I’ve always believed that when you’re in a touristy area, you’re better off searching for food off the beaten paths. So while walking down a smaller side street near the Spanish steps, I came across this custom tailoring shop.

Jaja has been around for almost 45 years, but changed ownership two years ago and is now run by Giuseppe Rossi. The shop’s front room is where he meets and fits clients, and all the shirts are made in the back. Giuseppe does all the custom pattern making and cutting, and he and three of his tailors do the sewing.

Since everything is bespoke and handmade, they only produce four shirts a day. Hand-sewn seams go around each of the armholes and down the plackets, and distinctive mother-of-pearl buttons slide through the handmade buttonholes.  The side seams, hems, and collars are made by machine, but they’re done with such a high stitch count (nine per centimeter) that they’re barely perceptible.

Signore Rossi was nice enough to demonstrate for me some of his handwork. Taking one of his current client’s shirts, he slowly and patiently hand stitched up the placket. As he later showed me, monograms are also genuinely hand embroidered, which you could tell by examining the back of embroidered fabric. Truly hand-embroidered monograms lack the small piece of fabric on the back that’s attached on machine embroidery to prevent wrinkling.

Prices for custom shirts start at $260, and go up from there depending on the detailing and fabric. Due to how much work is involved in cutting the first pattern, there is a minimum three shirts for the first order. Jaja can also make boxers out of their Italian shirtings for $50, as well as pajamas out of soft cotton flannels for $235. Looking back, I wish I had ordered a couple of monogrammed boxers. Who can’t use a pair of Italian boxers with a shadowed monogram?

Jaja Camiceria
Via Belsiana 7A
Rome, Italy

Signore Rossi stitches a placket.

Handwork on a Jaja placket.


Bolts of fabric at Jaja.


Collar styles at Jaja.




Hand-embroidered monogram from Jaja.


A man is not fully dressed until he has a pocket square in his pajama pocket.


Embroidered boxers--better than writing your name on the waistband with a sharpie.

All photos and text by Derek Guy. Check out Derek’s other sartorial endeavors at Die, Workwear and Put This On.