Six Great Types of Shirts for Fall

For nearly a century now, the most basic dress shirt for men is a solid white or light-blue button-up, made from 100% cotton, and usually coming in a plain or twill weave. It’s the default choice for dress shirts – something you can rely on year-round to look decent and acceptable, and is very rarely the wrong choice, assuming you’re dressing classically. 

There are times, however, when choosing something a bit different can yield a more harmonious look. Take, for example, the advantage of combining an airy, light-blue linen shirt with a tan cotton sport coat. The two textures are equally casual, and together, they lend a better presentation for summer. Similarly, a fine cotton dress shirt can look puny when set against a hardy Shetland tweed or mid-waled corduroy jacket. Better to pick something with more texture and “weight,” such as these following options, which I think make for excellent fall and winter shirts.


At the top of the list are flannels, which can come in a variety of forms. They can be solid or patterned (if patterned, usually checked), and made from either a softly brushed pure cotton or some kind of wool/ cotton blend. Viyella is particularly famous for their flannel shirtings (the word “shirtings” means “fabrics intended for shirts;” it is not a synonym for the word “shirts”). You can find them at a number of places, such as Dann Online, J. Press, and O’Connell’s. I unfortunately can’t say how any of those fit, but my guess is “traditional.” If you have a custom shirtmaker, they may also carry Viyella fabrics, which you can ask for by name.

Bold cotton plaids

Bold cotton plaids are different from flannels in that they don’t have that soft, brushed quality. They’re smooth like a fine cotton dress shirt, but remain a bit more autumnal through their patterns. Our advertiser Ledbury carries some through their short-run collection (they’ve got more coming down the pipeline, as they’re releasing a new short-run shirt every day this month). Brooks Brothers also has some designs, though mostly in non-iron fabrics, and Gant Rugger might be a good option for younger men. For something more affordable, there’s J. Crew. Just wait for one of their many sales. 


Tattersalls are symmetrical, thin-lined checks, usually made up of two colors for the lines and a plain-colored background. I find they’re a nice compromise between the dressiness of a standard dress shirt and the casualness of a bold cotton plaid. For something dressier still, you can go for a graph check shirt, which is exactly what it sounds like – a shirt with a pattern that looks like graph paper. Either would do well underneath a tweed or corduroy jacket, and you can find them at places such as Ralph Lauren, Brooks Brothers, and TM Lewin.

Oxford Cloth Button-Downs (aka OCBDs)

OCBDs are versatile enough for year-round wear, but also have the weight and texture necessary to look great underneath fall jackets. What’s not to like? You can read my long-winded series about them here, or just skip to my recommendations.


Another good year-round shirt that really comes into its own during the fall and winter seasons. You can find nice high-end options at Self Edge, Rising Sun, and Blue in Green. Mr. Porter also has some designer offerings, and J. Crew is again good for something more affordable (just wait for a sale). My favorite, however, is by Mister Freedom. I appreciate the emphasis they put into beautiful fabrics, and have found mine to age exceptionally well. When choosing one, keep in mind the kind of outerwear you might want to wear. Very casual chambray shirts with extra detailing should be kept with very casual outerwear, rather than traditional sport coats. 


Corduroy shirts are less versatile than any of the above options, but they’re nice to have if you’d like some more variety. Our advertiser Ledbury has one in brown coming out this month (it’s pictured above) and I like that it has a traditional looking collar and lowered second button (good for when you’re wearing the shirt casually and don’t want it buttoned all the way up). For something available now, there’s Michael Bastian, Beams Plus, and LL Bean.

Madras Shirts for Summer

I love madras - the colorful, airy fabric named after the Indian city from which it originally came. The stuff is lightweight and very breathable, which means it makes for the perfect summer shirt. Madras shirts are a wonderful accompaniment to trousers or suits made from cotton or linen, and of course should be worn with summer appropriate footwear, such as loafers or suede bucks. Unfortunately, good madras shirts are hard to find these days, and not because all the new stuff is colorfast, instead of bleeding and fading easily like the ones from yesteryear (for that truly dégagé look). Rather, it’s because most don’t fit me well or they lack the design details I want. 

My solution has been to get ones custom made. You can buy madras fabrics online through Atlantis Fabrics. They have two web pages - here and here - dedicated to them, and many are just $6 a yard. Given that the average sized man only needs about two yards per shirt, that’s just $12 for materials.

You can also check fabric stores to see if they have anything suitable. Above are some swatches from Rosen & Chadick, a fabric shop in Manhattan. Though they’re in New York City, they’re more than happy to send out fabric swatches for free. After you’ve figured out what you want, you can call them and pay for your order with a credit card. Most selections are $15 a yard. 

Once you have your fabrics, you’ll need to find a shirtmaker who is willing to take them from you. If you don’t have someone local you can go to, I recommend Cottonwork. They can custom make something to your body measurements or, if you’re hesitant about the process, they can copy any existing shirt you have. Just send them your best fitting shirt along with any notes about things you’d like tweaked (if any). They charge about $45 per shirt if you’re supplying the fabrics. 

If you’re reluctant to go the custom route, there are a bunch of ready-to-wear companies you can consider, such as O’Connell’s, J PressBrooks Brothers, and Dann Online. Some of these will fit quite full, such as the ones at Dann Online, while others can be very slim, such as Brooks’ Extra Slim Fits. 

You can also check out Gant Rugger and Ralph Lauren. Gant Rugger’s shirts are very slim and mostly meant to be worn untucked, while Ralph Lauren has the fuller ”Classic Fit” and slimmer “Custom Fit.” Finally, for something cheaper, try J Crew. In the past, they offered disappointingly drab designs, but this season’s are pleasantly colorful (as madras should be). If you wait till the end of the season, you can easily find their madras shirts discounted by 40-50%. 

(Cottonwork will be a Put This On advertiser next month, but our advertising and editorial processes are separate. - Jesse)