Few pieces work harder than the shirt on your back. Literally. As guys, we know all too well that a good shirt can make or break a fit. Too thin and it’ll leave very little to the imagination, too thick or shacket-like and you risk over-perspiring, and nobody wants that. Surprisingly, the perfect middle ground is wool, which is apt news considering wool shirts are becoming quite fashionable. Convenient, right?
Wool in general is getting around these days, creeping into categories it wouldn’t have dared touch before. I’ve currently got my eye on a pair of wool cargo pants of all things, because apparently that’s where we’re at now. But hey, that’s a story for another day. Today’s agenda is why, as good as a 100% cotton button-up is (and they’re pretty darn good), it pales in comparison to its freshly shorn cousin. Baa-rilliant stuff, really.
Not to brag, but I am somewhat of a woolly shirt connoisseur, and I can tell you they’re not all cut from the same cloth. Some are too long, and I find myself constantly folding the hem up, which is beyond annoying; others are too structured or just plain awkward. Luckily for you, I’ve eliminated those ones, and what we’re left with are the top-tier winter shirts worth the wool they’re made of.
The 4×4 One
Sage Nation’s sought-after chocolate brown Aviemore Parka has been sitting on my wish list for a while now, and until I nab one, this lambswool shirt will fill the void nicely. The cropped fit and double flap pockets give it a utilitarian edge, while the coal gray wool makes it a little less predictable than your standard button-up. Safe to say, the London-based brand, which draws on its founder’s Japanese-British heritage, is giving me plenty of reasons to keep that wish list growing.
The Familiar One

Willy Chavarria makes clothes for men who have no interest in dressing small, and apparently that applies to a checked shirt, too. This brushed virgin wool number takes the old-reliable flannel and gives it the Chavarria treatment, with a relaxed shape that feels more considered than your average lumberjack uniform.
The Under-the-Radar One

This lighter take on the hefty shirt is well and truly calling my name. It just looks like one of ’em you’ll never want to part with. It’s not a full-blown wool shirt, but the fuzzy marl finish gives it that woolly, lived-in look without all the extra heft. Think of it as the workwear equivalent of your favorite old sweatshirt, only with a collar and a couple of pockets for good measure. Sells itself, really.
The Sartorialist One

The beauty of these “wool flannels” is that they can just as easily pull double duty as a jacket, too (rain-dependent). Evan Kinori has been doing this sort of thing for years, and it’s part of why his work has become such a reference point for people who care about good wool and clothes that actually get worn. Sure, it looks like something your granddad might have worn, if your granddad happened to have excellent taste and a healthy clothing budget, that is.
The High Street One

Like the modern day fleece, a hefty price tag and a premium product don’t have to go hand in hand anymore. COS is case and point. This double-faced wool overshirt proves you don’t have to blow half your paycheck to get your hands on a decent wool layer. The mauve shade is a nice change of pace from the usual suspects, too, and gives the otherwise understated design a bit of personality.
The Everyman One

The A.P.C. Malaury is the sort of checked shirt that makes you wonder why you don’t wear more checks (I know I am). The light gray pattern is easy enough to throw on with pretty much anything, but the real selling point is that it looks just as good tied around your waist. You know, for those moments when your outfit needs a little something extra and you can’t quite put your finger on what. This is what.
The Minimalist One

Some shirts just have an air of sophistication about them, and ssstein’s taupe number has it in spades. Cut from extra-fine wool, it has a lovely fluid drape that gives the oversized fit a more polished feel without losing its nonchalant appeal. The muted taupe helps, too, giving it a richness that’ll smarten up any downstairs situation.
The Heavyweight One

Lately, I can’t help but gravitate toward checks. Maybe it’s the time of year, maybe 25 is when you start getting excited about a good pattern. Either way, I’ve just found a more winter-friendly version, courtesy of Octobre Éditions, no less. The Lars overshirt swaps your usual flannel for a blue, beige, and navy tile pattern, all in 100% wool. And just like that, I’m looking at my other shirts a little differently.
The Swanky One

Yes, it’s an eye-watering amount of money for a shirt, but then again, it’s Prada. The Italian house has a knack for making everyday pieces feel like something worth getting excited about, and this wool zip-up is no exception. The usual buttons are out, replaced by a zip fastening that gives it more of a workwear feel, while the drawstring hem adds a touch of extra shape. Look, nobody ever said having good taste was a cheap hobby.
Some Strong Contenders:
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