We were waiting for this collection ever since Sperry announced that they'd made the Blackstock & Weber founder their new creative director. Echevarria didn't disappoint with his first collection and, if you ask us, these were the star of the lineup. This archival design was the original shoe design produced by Paul Sperry, but it's been updated for 2024 in a tonal colorway, cut from premium “hairy suede”, which looks (and feels) even better in person. Handcrafted in Maine, they're finished with a Vibram lug sole and will look just as good with your winter wardrobe as they will come spring.

In theory, you might not think this would work. It's like the lovechild of a sneaker and a Wallabee. But the moc-toe construction of this Saucony Shadow, finished with a gum wrapper sole, feels very fresh. It's half moccasin, half sneaker, and a 100% game-changer. And bonus, it's now on sale.

Has all this bad weather lately made you rethink your current boot lineup? It certainly has us looking for even more sturdy (and warm) options, which led us to L.L. Bean's newest take on their signature Bean Boots. The Engineer style is lined in premium flannel, insulated for extra-cozy warmth and handsewn in Maine. Plus, they look as good with everything from jeans and chinos to workwear pants.