The Best Shoes of 2020
Comfort and style as you go from lift lines to bar limes
For exclusive access to all of our fitness, gear, adventure, and travel stories, plus discounts on trips, events, and gear, sign up for Outside+ today.
Birkenstock Tokyo Teddy Shearling ($220)
After a day on the slopes crammed into boots that “fit,” sliding your aching feet into these feels like a spa treatment. The wool-lined forefoot is roomy, and the aged-leather upper looks right at home when you’re sitting by the fire with hot toddy in hand.
Vans City TRL ($110)
This is the footwear equivalent of Corbet’s Couloir: strictly for the confident and daring. The overbuilt rubber outsole is a mash of cross-hatching and rubber nubs, while suede overlays stack atop still more overlays. An aggressive external heel counter wraps to the midfoot. Experts only.
OluKai Nalukai ($140)
Leather boots typically foster sweat and stink, but the Nalukai keeps both at bay with its moisture-wicking, antimicrobial liner. Outside, a full-grain leather upper channels classic mountain-town aesthetics. We loved the podlike design of the outsole, which adds traction without weighing you down.
Merrell Ontario x SK Wax ($160)
From its home in the Midwest, hatmaker Stormy Kromer has been shielding the noggins of outdoor enthusiasts for over a century. Merrell’s collaboration, the Ontario x SK Wax, makes good use of this expertise with a paraffin-treated cotton upper and flannel lining. The Vibram Megagrip outsole and reinforced leather accents make this vintage-inspired hiker even more winter-ready.
Chaco Dixon High ($165)
Is the Dixon a running shoe? The EVA-foam cushion and wave-patterned rubber outsole would indicate so. Surely it’s a boot, though, with waterproof leather rising up past the ankle to seal out winter drafts. However you choose to categorize it, this Franken-footwear was made for the mountains.
Wolverine 1000 Mile Original Sneaker ($285)
A variation on Wolverine’s über-popular 1000 Mile Boot, this mid-top sneaker is made from waterproof Horween leather and has a flexible Vibram outsole that will help you arrive at the bar without looking like you traversed a glacier to get there.