The North Face Best Stylish Winter Jackets

When it comes to selecting a versatile and timeless puffer, there are a few design elements you’ll never go wrong with. Look for a silhouette that hits mid-thigh with a hood, elastic cuffs, and zips at the top and bottom. This classic has all that and more (the “more” in this case being wind-resistant and water-repellent material).

When outfitting for a day in the frosty snow or otherwise enjoying the winter sun, a sport-inspired parka is a good bet aesthetically and functionally. This one is made with the label’s recycled and waterproof DryVent fabric, and designed with space to spare—so you can pile on the layers underneath (and peel off as you fit in run after run).

Speaking of those layers, the coziest winter outfits always include a good vest. A mixed fill of down and synthetic fibers is warm but not too bulky. Style this over or under everything in your cold-weather closet; it’s sporty by nature but equally chic over cashmere or a classic button-down.

Gift this to the guy in your life—or pull it on yourself for a stylishly oversized fit. Ribbing at the cuffs and hem speaks to an old-school varsity fit while also keeping the chill at bay. Add welted hand pockets, recycled-down fill, and a faux-fur accent, and you have warmth personified.

Jetting off somewhere fabulous where the weather is unpredictable? The smartest topper is something warm but slim, and this ultra-thin zip-up is that in spades. It’s designed with four-way stretch, and it tucks into an envelope-size pouch that will fit in the tightest of carry-ons.

Remember those biting days in the past when you stole that bigger, heavier coat hanging in the closet? Well, why not invest in one of your own? Designed for men, this warm pick looks good on slimmer frames, too, and is more than ready for the cold. It’s windproof and waterproof with pockets galore, including two front patch pockets that can stash necessities for whatever run you’re on.