The Best Winter Menswear for 2026, From Long Johns to Shearling Coats

If the phrase “Long Johns” puts you in mind of the scratchy, woolly underwear worn by a cartoon lumberjack, then allow us to introduce you to this thoroughly 21st-century update by CDLP. Made from a blend of soft merino and lightweight, breathable lyocell, they feel like silk but warm like wool.

Leon Leonwood Bean was on to something when he created the first Bean Boot in 1912, with the express purpose of keeping his feet warm and dry while duck hunting. The rubber-bottom, leather-upper style is just as suited to ice-slicked streets thanks to the chain-like grips of its outsole, and a shearling-lined iteration is insulated enough to withstand winter’s very worst.

The magic of flannel lies in its finishing, which creates a raised “nap” of gently teased fibers, trapping heat. It’s an insulating effect you can enjoy from head to toe in this chalkstripe J. Press suit, made with flannel sourced from the renowned English mill Fox Brothers.

Going about your day with a heavyweight cashmere blanket draped around your shoulders isn’t particularly practical. The next best thing is slipping into this 4-ply cashmere shawl-collar cardigan, made in Scotland for the Armoury, which is like a blanket with sleeves and buttons.

First worn by English polo players to warm themselves between chukkers, the polo coat might be considered the most casual of formal overcoats, or the most formal of casual overcoats. The Anthology’s iteration, made with menswear writer Simon Crompton, checks all the boxes, from its turnback cuffs to oversized “postbox” pockets, and perhaps most importantly, is made from genuine camelhair. Its generous peaked lapels can be folded up and sealed with a hidden button below the chin, eliminating the need for a scarf.

Sunspel offers a gentler take on the crewneck Shetland sweater, making its version from super Geelong lambswool. Each is made in Scotland, where a wash in pure local spring water softens the yarns even further.

Duffle coats were worn by Royal Navy sailors serving in the North Atlantic during WWII, where weather conditions might be described as “inclement,” to say the least. Following the war, Gloverall transitioned from selling surplus duffle coats to manufacturing its own, including the “Monty” model, named for the conflict’s most celebrated British commander. Fabricated from a weighty wool-blend and deliberately oversized to allow for plenty of layering beneath, it remains a wintertime staple to this day

Yet another item relied on by Royal Navy sailors in freezing conditions, the peacoat is championed today by Private White V.C. The British label fabricates its seaworthy version from an ultra-heavyweight, 30-ounce Melton wool woven in England that can withstand wind and light rain.

Rubato’s Explorer rollneck is a throwback to an era before technical clothing, when mountaineers and Arctic pioneers had to rely on knitwear. Made in Scotland from a chunky, 4-ply merino-cashmere blend and cut on the generous side, it performs today under a parka or even a double-breasted suit.

A descendant of the 19th-century Long John, thermal shirts gained wider popularity in World War II, where they were worn by U.S. servicemen as an insulating base layer. The same utility applies to this long-sleeved thermal tee by Buck Mason, made from waffle-knit cotton with a smooth jersey back for greater ease when layering.

From the outside, Quaker Marine’s Ausable Pant looks like just another chino. But what really matters, as always, is what’s on the inside, in this case, a 100 percent cotton flannel lining.

A sheepskin coat is among the warmest things a man can wear, and you’re getting more than four pounds of it in the form of Overland’s Maverick. A traditional rancher coat with deep front pockets and a collar that turns up against the wind, it has the added bonus of making you look like a cast member of a Taylor Sheridan production.

These proper dress gloves by Hestra are cut and sewn by hand using hairsheep leather in the brand’s Hungarian workshop. Each finished glove is lined with cashmere, which you’ll actually be able to feel as your hands won’t be numb.

The humble flannel shirt has been absolutely love-bombed by Drake’s, who pulled out all the stops when making their own version: brushed Japanese cotton, a single-needle construction, a stand collar with a floating interlining, and two button-flap chest pockets.

The great, late Glenn O’Brien once said that the easiest way to feel like a millionaire was to spend $100 on cashmere socks. American Trench’s Oxford sock—which is priced $5 below O’Brien’s estimate—also carries the advantage of better warming your feet.


Not all beanies are created equal. Case in point: this N. Peal cap, which is made from 100 percent organic, 4-ply cashmere with a fold-down cuff to better protect the ears.

Sometimes, the best remedy to wintertime is to stay indoors—particularly if you can do so in these cashmere lounge pants by Begg & Co. Made of finer, 2-ply cashmere, they’re exceptionally light and soft, and precisely what you want on your lower half during your next Netflix binge.

You don’t want to skimp on a scarf when the temperature is in the single digits, and that brings us to this cashmere number by Johnstons of Elgin. Generously oversized and finished with fringe, it bears the traditional tartan of Clan Buchanan, whose Highland history stretches back to the 13th century.