As the temperatures drop, layering becomes a more important element every day. I am always happy to return to my heavier winter button downs, and in late November when the reality sets in that it’s going to be cold and dark for the next four months, it’s comforting to have a trusty flannel shirt for when you want something substantial and warm to layer. Whether it’s a wool or cotton flannel, chamois, or heavy twill fabric, it’s likely to be soft and feel like a blanket when you wear it.
I had a slightly delusional moment while I was researching these shirts that involved me almost buying every one of them. Something about the fabric and it being below freezing outside and pops of color and layering combined into me thinking that it was totally OK to buy shirts, because I’m going enjoy having them, and that’s enough of a reason, right?
1. Gant Rugger The Woolster E-Z Original Button Down
Gant Rugger has a wide variety of fabric weights and patterns, and their fall shirting won me over a couple of years ago when I felt their cotton twill in person. There’s also something to be said about a shirt cut that accommodates all sorts of body types. When you talk to guys about how they prefer their shirts to fit, it’s fascinating how many nuances there are. Sleeves that are too short, narrow shoulders, and high arm holes, in any combination, seem to thwart many guys from finding the right shirt. However, Gant Rugger’s E-Z fit seems to bypass all that and is just a good fitting shirt for a variety of body types. The wool flannel seals the deal.
2. Pendleton Trail Shirt
There’s something to be said about a known quantity. Pendleton has been turning their impressive woolen fabrics into blankets, shirts, pants, jackets, and a lot more for longer than any of us have been alive, and it’s good stuff. This Trail shirt had me for its details: 10 oz heathered Umatilla wool, suede elbow patches, and button chest pocket. I love a versatile shirt, and this one fits the bill – you could wear it on its own, or as an overshirt or shirt-jacket, and you can be certain that it’ll be a fixture in your winter repertoire for a long time.
3. Five Brother Flannel Work Shirt
Five Brother shirts have been around since 1890. The brand, started in New York State, produced high-quality workwear for years and years, but faded away in the 20th century. Recently, Five Brother was reintroduced by a company based in California dedicated to superb reproductions of their shirts. Almost everything is the same, and that’s great – the cotton flannel is hard wearing, and the plaid patterns have interesting color combinations so you can remind yourself that there are other colors besides gray and gray come February.
4. Taylor Stitch Yosemite Shirt
I’ve been really high on Taylor Stitch’s clothing lately. In my researching items to list on this website, I often seem to find myself at back at their website, trying to pick which piece to write about. This Yosemite Shirt is a bestseller of theirs, and has just been restocked, so I’m glad this winter shirting post coincides with it being available. This is the last run of these shirts for the year, so if you’re looking for a chamois shirt with nicely shaped chest pockets and a soft hand, look no further.
5. Gitman Vintage Navy Flannel Fleck Shirt
I couldn’t write about winter shirting without including a Gitman Vintage flannel in the list. I own one of their flannels and I’d throw it on every day if I could. It’s a heavy but supple Japanese cotton that gets more luxurious with every subsequent wear. These shirts are fit a little more loosely than Gitman’s oxfords and poplins, but they still have the same appealing silhouette. This navy check option with multicolor dots (like a Donegal tweed almost) would make anybody look good, and pulling it out at the beginning of every year will be like seeing an old friend for the first time in too long.