Winter Outfit Ideas For Men | Winter Fashion

If you’re north of the Equator, late October is a blessing and a curse. On one hand, men’s fashion is built around layering – whether you err towards J.Crew or Supreme, the cold weather months mean sartorial freedom.

On the other, those first frosty mornings mean only one thing: slowly, surely, winter is coming. With snow just around the corner, brush up your seasonal style with these 9 Cold-Weather Essentials.

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Winter Outfits

With winter being built around layering your outfits together, it can be a little difficult to put together your own fits if you’re not used to it. With these casual winter outfit ideas for guys you’ll have a pretty good idea on how to dress for winter. From how to wear puffer jackets, to fish tail parks, to a casual overcoat, we’ve covered it all here.

Winter Clothing Checklist ✔️

Wool Overcoat

Our pick: L’ESTRANGE – The Modular Coat

The outerwear choice of both traditionalists and Hypebeasts alike. And who could blame them? Long lines, minimal detailing, and a rakish silhouette make your standard wool overcoat a versatile, stylish choice.

Plus, thanks to the natural moisture-wicking properties of wool, an overcoat makes for a great snow-ready layer if technical coats just aren’t your style.

Selvedge Denim Jeans

Our pick: ASKET – The Raw Denim Jeans

For men, cold-weather style is all about texture. Case in point: selvedge denim jeans. Compared to your standard “mall brands,” most companies producing jeans made from selvedge will forgo abrasive chemical washing processes, choosing to either lightly-wash their denim (balancing rugged looks with fabric comfort) or even leave it 100% “raw” (going full-tilt burly, break-in required). Coupled with the sealed “self-edge” inside the hem of every pair, these sturdy selvedge jeans offer durability, style, and thick fabric to block out the coldest winter winds.

Beanie Hat

Our pick: ISTO – Black Beanie

It’s a simple concept: take warm wool, knit it into a hat, and cover your head. Boom. Instant winter headgear. Thanks to its utter clarity, tracing the singular origin of the wool beanie is difficult. Both Andean nomads and Irish fishermen alike independently developed simple wool hats centuries – and continents – apart.

This convergent evolution has left our globalized world with a kaleidoscope of beanie styles, sporting everything from ear flaps to pompoms and sigh even beards. However, for warmth with style, minimalism is your friend. The traditional “dock worker” beanie (thick knit, tight fit, no B.S.) is a staple for a reason.

Leather Boots

Our pick: VELASCA – Pastissee Leather Boots

The foundation of any fall/winter wardrobe. With millennia of refinement in every stitch, the classic smooth leather boot is the perfect choice for functional (and stylish!) cold-weather footwear.

And I do mean essential. Simply put, there is no reason for men living above the Tropic of Cancer to not own a pair. With thousands of styles and brands available, there are leather boots on the market that will fit your style. Prepster? Allen Edmonds. Streetbeast? Timberlands. Ethically-opposed? Vegan leather. If you choose nothing else this season, make it boots.

Weather-Ready Sweats

Our pick: CDLP – Heavy Terry Sweatpants

When the temperatures drop, it’s only natural to reach for a cozy pair of sweatpants. If you never plan on going outside, those oversized cotton fleece sweats from college should work great!

But when Cabin Fever sets in (or the gym comes calling), you’ll be happy you went for something with an ounce more tech. Not only are they great insulation from the cold, but tapered technical sweats also provide a street-ready replacement for chinos in case your winter look calls for sneakers. For stylish all-weather versatility, technical sweats just can’t be beat.

Cable-Knit Sweater

Our pick: AURELIEN – Cable Knit Sweater

It’s no surprise that Northern Europe knows how to dress for the cold. Exhibit 1: the cable-knit sweater. First made famous by fishermen braving North Atlantic swells, these intricate sweaters (originally called “Aran” knits, after their place of birth, the Aran Islands) have become a sartorial staple for men all over the world.

While cable-knit sweaters come in a variety of forms, the iconic “fishermens sweater” of old refers to crewneck sweaters made from thick, ropy lambswool. Our recommendation: either go for the classic, or try a shawl collar cardigan to show off your layers.

Wool Socks

Our pick: Darn Tough – Merino Wool Socks

Below freezing, details matter. Even through the thickest leather boots, your little piggies will be gone to market unless you’ve got some serious sock support. While nothing beats Grandma’s crocheted stockings, chunky rag-wool socks from brands both American and Japanese will fight off frostbite with flare.

Bomber Jacket

Our pick: UNRECORDED – Recycled Bomber Jacket

No list of layers is complete without the venerable MA-1. Crafted from flight-ready nylon, the MA-1 Bomber Jacket is one of the most iconic pieces of outerwear in the world. Heat-reflective insulation, nylon shell, and a slim profile to boot: it’s a mil-surp standout turned streetwear staple.

While almost every line on earth offers their own bomber variation, we recommend the original Alpha Industries MA-1. Alpha earned its first Department of Defense contract just before the Vietnam War, and has continued manufacturing bombers in the nearly 50 years since.

Layer-Friendly Hoodie

Our pick: WAX LONDON – Hoodie

Last but not least: the venerable hooded sweatshirt. As a supplemental layer on those truly freezing days, nothing is better: a thick hoodie paired with any sort of weather-ready shell is an easy alternative to expensive and cumbersome down parkas.

To maximize versatility, stick to solid colors and heavy cotton fleece – anything below 200g/mis best kept for spring.