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The cold season is here. Which means it’s almost time to bundle up until you’re nothing more than a head poking out from beneath many layers of down, wool, and shearling. That may sound tempting, but winter jackets are a difficult look to nail. Some people prefer a concealed layering approach to the extra-large silhouette, while others anxiously await any opportunity to go big with their outerwear.
With this divisive winter wardrobe staple on the menu, I decided to take a close look at some of the greatest winter jackets, compiling a list of what I think to be the best winter outwear options. From The North Face to Casablanca, these jackets will keep you warm and comfortable this winter while also giving you some gram points. When done correctly, style and functionality can coexist wonderfully.
Canada Goose Chilliwack Bomber Jacket
Developed as a nod to post-war bush pilots in Canada’s North, the Chilliwack Bomber provides the durability, warmth, and mobility that these pilots needed when working on Arctic runways. An enduringly popular and iconic style, the Chilliwack is one of Canada Goose’s most beloved jackets. Customize your parka and extend the coverage of your hood with a variety of the brand’s interchangeable Hood Trim accessories.
Canada Goose: $1,170
The North Face 1996 Retro Nuptse Puffer Jacket
Built for mountain- and city-life, this retro Nuptse jacket that has a boxy silhouette, original shiny ripstop fabric, iconic oversize baffles and stowable hood will keep you warm and dry when it gets cold and wet.
Paragon Sports: $260
MAMMUT Stoney HS Thermo Jacket
Stoney HS Thermo Jacket Men. A perfect combination of weather protection and insulation. The jacket is made from 2-layer DRYtech material (water column: 20,000 mm), which keeps out snow and rain while remaining breathable. A detachable, three-way-adjustable hood, a concealed front zipper and splash-proof side pockets complete the weather protection. The synthetic Ajungilak OTI insulating fibers are impervious to moisture and keep you warm and dry, even on cold, wet days.
Paragon Sports: $390
Canada Goose Woolford Jacket
On milder days, reach for the Woolford Jacket, a hip-length bomber with military-inspired details. Double-stacked side-entry pockets allow for easy access to personal belongings without exposing hands to the cold. Soft, stretch rib cuffs comfortably hold warmth in.
Paragon Sports: $770
Neil Barrett x Penfield Puffer Jacket
Made in collaboration with Penfield – an outdoor clothing brand – this puffer jacket from Neil Barrett stands out thanks to its faux-shearling and suede trims. The design appears in a versatile black tone and features a signature Bolt Badge at the sleeve.
Farfetch: $980
Casablanca Monogram Padded Puffer Jacket
Self-described as a ‘modern reimagining of the timeless apres-sport aesthetic’, Casablanca has mastered the fusion of luxury and leisure. Padded with a blend of feather and cotton, this puffer jacket boasts an understated monogram print and a quilted finish that accentuates its voluminous silhouette.
Farfetch: $1,870
The North Face Gotham Jacket III
Block out winter’s chill with this weatherproof jacket that’s insulated with warm 550-fill down insulation and features an adjustable hood, stormflap, and ribbed trim for complete coverage.
Paragon Sports: $300
The North Face Printed 1996 Retro Nuptse
The second you see the oversized baffles you know you’re looking at our iconic Nuptse Jacket. This Printed style draws inspiration from the 1996 version and has lofty 700-fill Down with a sleek, stowable hood.
Paragon Sports: $290
Moose Knuckles Shippagan Padded Jacket
You’ll huff, you’ll puff…and you’ll strut your stuff. But just because this puffer jacket from Moose Knuckles looks great on you, that doesn’t give you the right to blow down anyone’s home. Straw or not.
Farfetch: $980
Canada Goose MacMillan Parka In Black Label Print
This hip-length parka couples great warmth with stylized features including a quilt-through design and a new curved hemline. The MacMillan Parka provides fundamental protection for active city living despite the weather.
Canada Goose: $990
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