Last week’s post was all about the classics, but rainy, cooler weather has rolled into the midwest after a seemingly generational run of sunshine and comfortable temperatures, so my mind has turned to the cozy. After changing over my closet from warm-weather clothing to cold-weather, I uncovered some very cozy pieces I’d delightfully forgotten about until pulling them out.
Flannel and cashmere-blend shirting
What’s more cozy than a cotton flannel shirt in the fall? In plaid, they can be a fun way to wear color, though it’s also nice to wear solid colors to layer with other patterns and textures.
But besides plain cotton flannel, last year I was excited to add a Thomas Mason cashmere-blend flannel twill shirt to my wardrobe, and it’s one of my favorite pieces to pull back out when the weather turns cool. It’s not a brushed texture and is a medium-light weight, so it pairs better with dressier outfits—I wear mine under a sportcoat as well as under a sweater.
Links:
Proper Cloth Flannel shirt fabrics [MUSINGS10 for the 10% discount]—I have the Japanese flannel in Blackwatch tartan and love it
Proper Cloth cotton-cashmere flannel fabrics [MUSINGS10 for the 10% discount]
Luca Faloni cashmere blend shirts
Besnard MTM Thomas Mason shirt
Shawl collar cardigans and stand-up collar cardigans
The shawl collar is the ultimate cozy, but sometimes that’s a bit too much, especially if you want to wear it out and about when it may be prudent to layer under some rain gear. This is where cozy stand-up collar cardigans like Alex Crane’s kite jacket or Inis Meain’s pub jacket (pictured above) come into play. The stand-up collar can still cover your neck, but it doesn’t have the volume and bulk of the shawl collar in front.
Links:
Buck Mason shawl collar cardigan
Bleu de Chauffe shawl cardigan
Alex Crane kite jacket (stand-up cardigan)
Inis Meain cardigan (not the pub jacket but very similar)
SuitSupply funnel neck (not a cardi, but a pullover, but it looks really great so I’m including it)
Kent Wang shawl collar cardigan
The Armoury (in cashmere!) or in Lambswool
Flannel trousers (in a comfortable fit!)
Flannel shirts are obviously great, but how could it get better than pants made of flannel? Then again, in the slim fit days, I never was able to quite relax even wearing soft flannel trousers. How could I if sitting down wasn’t super comfortable? Now, as I’m favoring looser fits due to my body changing shapes as I age but due for the comfort factor, flannel trousers are a cozy, comfortable option I look forward to putting on.
Links:
Proper Cloth (my favorite for the ability to dial in my fit exactly as I want them)
Fawn, charcoal, medium and light gray [MUSINGS10 is the 10% discount code]
SuitSupply flannel straight-leg trousers
Spier & Mackay flannel trousers
Moleskin trousers
With a dense weave but soft, textured nap, moleskin is like the cotton fabric version of suede. It’s soft like velvet, but unlike velvet has a history associated with workwear garments and has less of a sheen. That’s why moleskin feels right as a 5-pocket pant instead of a tailored trouser, but if you got some in a traditional trouser, it would have a cool high-low vibe that would work great with tweed jackets and denim shirts.
Links:
J.Press moleskin trousers (not a full tailored trouser but more of a chino style)
Spier & Mackay moleskin chinos
Proper Cloth (I would customize these as chinos, as a best of both worlds blend to be dressier than 5-pockets while still being machine washable) [MUSINGS10 is the code for 10% off]
House of Bruar moleskin 5-pockets or moleskin dress trousers
Bill’s Khakis moleskin 5-pockets
Shearling-lined footwear
Primarily I’m talking about shearling lined slippers for wear indoors during the winter, but there are also shearling-lined boots for wear outdoors. One of the most surprisingly great additions to my wardrobe the last couple years has been the shearling lined zipper boots from Myrqvist. They’re perfect for popping outside to shovel the driveway, get the mail, or even short walks around the neighborhood. Otherwise during work from home days I wear LL Bean shearling moccasins. For a commute outside where you don’t want to change shoes, something like Meermin’s shearling lined boots could make sense.
Links:
LL Bean shearling lined footwear
Soft tees
At home, especially in the mornings before I get ready to go to work, I’m in a tee and one of those cozy cardigans I mentioned above. The tee itself is a major part of how comfortable I am, since it’s the layer that’s against my skin the most. Regular cotton tees are great, and of course there are super soft cotton tees, but recently I’ve been enjoying alternative blends. From the “mad scientist of cloth” (Mauro at Wolf vs Goat), comes a tee made of bamboo mixed with Sorona. It’s kind of a hard sell for some people in 2026, since Sorona is a Dupont product billed as kind of a polyester 2.0. But the tee’s outrageous softness speaks for itself (and Mauro says it’s a luxury fiber being used by the most expensive labels you can think of). The lightweight version is nicer and more comfortable in my experience, and the long sleeve version especially is ideal for cozy mornings. WvG is also selling cotton-cashmere tees, if you prefer to go the all-natural fiber route. His obsessive pursuit of the best qualities of whatever he can find means you know those are great, too.
Spier & Mackay’s cotton-modal tees have become another staple for me. Modal is less synthetic than poly, since it is derived from plant matter. The combo of modal with cotton makes it very soft, color-fast, and unlike pure cotton it doesn’t lose shape with wear. Those qualities, by the way, make cotton-modal boxer briefs my favored underwear for the last half decade.
Links:
Spier & Mackay cotton-modal tee
Quince cotton-modal tee (haven’t tried these specifically but worth the price to give them a try)
Cashmere sweaters of all varieties but especially turtlenecks
The cashmere crewneck in navy is my single go-to, particularly to wear over button up shirts, though I also wear it with just a tee casually under other layers. But the turtleneck—or roll neck, or maybe a mock neck—in cashmere is the next level up. It speaks louder than just a crewneck, and obviously keeps you warmer as well.
The thing about turtlenecks though is that if they are made of a fiber that’s scratchy in the least, they’ll bother you all day long. Which is why cashmere is the move.
Links:
Proper Cloth cashmere turtleneck [MUSINGS10 for the 10% discount]
Inis Meain turtleneck (the chunkier ones are so awesome as statement pieces)
Todd Snyder silk-cashmere turtleneck
Sid Mashburn escorial wool turtleneck (the next best thing to cashmere)
Suitsupply cashmere turtleneck
Sid Mashburn cashmere crewnecks
