GearApparel
2020 Winter Buyers Guide

The Best Shoes of 2020

Comfort and style as you go from lift lines to bar limes

(Photo: Inga Hendrickson)
outside

When you buy something using the retail links in our stories, we may earn a small commission. Outside does not accept money for editorial gear reviews. Read more about our policy.

Birkenstock Tokyo Teddy Shearling ($220)

outside
(Photo: Inga Hendrickson)

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.

Buy Now


Vans City TRL ($110)

Shoes
(Photo: Courtesy Vans)

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.

Buy Now


OluKai Nalukai ($140)

Shoes
(Photo: Courtesy Olukai)

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.

Buy Now


Merrell Ontario x SK Wax ($160)

Shoes
(Photo: Courtesy Merrell)

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. 

Buy Now


Chaco Dixon High ($165)

Shoes
(Photo: Courtesy Chaco)

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.

Buy Now


Wolverine 1000 Mile Original Sneaker ($285)

Shoes
(Photo: Courtesy Wolverine)

A variation on Wolverine’s ├╝ber-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.

Buy Now

From Winter 2020 Buyer's Guide
Filed To: BootsFootwearStyleClothing and Apparel
Lead Photo: Inga Hendrickson
More Gear