See more of the best puffer jackets for men
The North Face 1996 retro Nuptse jacket
The North Face
Patagonia down sweater hoodie
Moncler Cevenne garment-dyed quilted shell down jacket
Arc’teryx Thorium AR hoody
The Trench Coat
If raincoats were a group of friends, the trench coat would be the chic one from Paris. It’s always dashing, whether it’s pouring rain or mildly breezy, paired with a suit and brogues or a T-shirt and trashed jeans. A classic tan trench never misses, but you can always opt for a slick black version or even a boldly patterned number for even more flair.
Burberry Kensington classic trench coat
American Trench coat in dark navy Ventile
Uniqlo U single-breasted trench coat
C’H’CM’ short rain mac
The Fleece Jacket
Ever looked at a sheep and thought, Boy, I wish I felt that cozy and comfortable? Now you can. A gorp-y, high-quality fleece jacket won’t just help you texturize your fits and pack in the warmth—either as a top layer in the spring and fall or under a coat in the winter—they’re also surprisingly great for battling the elements. In fact, Patagonia founder Yvon Chouinard first fell in love with deep pile fleece for its ability to repel moisture and block out harsh winds.
See more of the best men’s fleece jackets
Patagonia classic Retro-X fleece jacket
Uniqlo fluffy yarn fleece full-zip jacket
Gap reversible fleece jacket
Manastash “Mountain Gorilla” fleece jacket
The Bomber Jacket
The bomber jacket was originally designed for high-altitude missions during World War II, but it’s enjoyed relevance on the ground ever since. The real-deal versions are built tough and warm enough to keep pilots comfortable in the cockpit, of course, but the true key to the bomber’s appeal is its cropped and roomy silhouette, which lends it a flatteringly relaxed vibe that’s perfect for layering. Tack on a pair of well-heeled boots, and you can’t help but feel like you’re on cloud nine.
Alpha Industries MA-1 flight bomber jacket
Todd Snyder + Champion Brooklyn Circus knit bomber
Everlane bomber jacket
Thom Browne tricolour-stripe cotton-blend bomber jacket
The Waxed Cotton Jacket
Picture a swaggy old Briton roaming the countryside, his trusty Airedale Terrier at his side. What is he wearing? Corduroy pants and brogue boots, probably, all topped off with a hardy waxed cotton hunting jacket. As far as sheer rugged elegance goes, it’s impossible to top waxed cotton’s indelible mix of weather-resistance, durability, and handsomeness. These jackets are built to last a lifetime—long enough that someday you’ll look like that swaggy old Briton donning it.
Barbour classic Bedale wax cotton jacket
Flint + Tinder flannel-lined waxed trucker jacket
Buck Mason dry waxed highland jacket
Belstaff Trialmaster logo-appliquéd belted waxed-cotton jacket
The Work Jacket
These jackets range from the barebones to the over-engineered, but are all designed to take on tough tasks. They’re generally cut with roomy and at hip-length for increased range of motion, which makes ’em ideal for pairing with high-waisted, wide-legged pants. Like trucker jackets, work jackets earn their beauty through hard work and wear.
Dickies insulated “Eisenhower’ jacket
Carhartt WIP “Detroit” jacket
Rag & Bone “Stark” cotton twill jacket
Rag & Bone
Bode vintage-patch corduroy jacket
The Parka and Anorak
Prefer a hood with your outerwear? Anoraks and parkas will keep your noggin high and dry in a pinch, when you’ve left home without a beanie or an umbrella. Thanks to their outdoorsy and military backgrounds, respectively, they possess all the function and versatility you could possibly need in a casual jacket.
Battenwear light shell parka
Junya Watanabe Man backpack parka
Low stock — but might be OK to keep anyway if you can’t find replacement
Uniqlo cotton parka
Marmot PreCip eco anorak
Might be one too many Arc’teryx jackets if we’re also putting them in puffers and rain jackets? Can we find something to replace at least one of if not two?
When you need to look truly refined and polished in the dead of winter, a topcoat is the only way to go. All of that extra length will give your fits some gorgeous flow and drape, and will also provide plenty of extra real estate for a textured or patterned fabric to really make an impact.
Abercrombie & Fitch double-breasted wool-blend topcoat
Abercrombie & Fitch
Club Monaco mélange wool-blend coat
Feels more like a trench than a topcoat?
Sasquatchfabrix satin-belted double-breasted wool-blend coat
Drake’s taupe Glen check casentino wool blend raglan sleeve overcoat
The Golf Jacket
Looking for something lightweight and slightly preppy? Try a golf jacket. You might know them as a Harrington or a Drizzler, but the concept remains the same: a lightweight poplin or twill shell with a short body, elastic waist, and a collar that you can button up to cover your neck on chillier occasions. They’ve got British roots—hence the traditional tartan lining—but hit the mainstream stateside in the ‘60s and ‘70s thanks to fellas like Elvis, James Dean, and Steve McQueen. Zip one up over a polo and pressed slacks for a classic look, or go full British mod with slim jeans and shiny work boots.
Baracuta G9 classic jacket
London Fog “Auburn” zip-front golf jacket
Neighborhood drizzler jacket