This breed of footwear can skew punk, outdoorsy, or utilitarian, depending on the pair you choose and what you choose to wear it with. I have a pair I wear a lot this time of year—you can at least partially winterize them by shelling out for shearling insoles. I like the clunky sole and orange laces on this pair from Italian brand Diemme.
You can’t go too far wrong with a pair of Doc Martens, and they’ll last forever.
I dig the sneaker sole and blushy hue on these, from Rag & Bone.
I wish this Tory Burch pair didn’t have the logo stamped on it, but I’m willing to overlook it because they’re so good: I’m a sucker for cracked leather, and I like how they deployed the fleece.
A polished and well-priced boot from Sam Edelman.
For those who require a platform sole, I bring you this.
These have a hint of a platform too, and they look like they’d be perfect with jeans.
This one is from Birkenstock, and I frankly don’t just love the way it looks, but it must be the soul of comfort.
These are from La Canadienne, a brand that’s serious about foul-weather boots, and they’re marked nicely down.
This Madewell pair has a menswearish vibe I like.
I know these are slightly nuts, but I also find them completely adorable.
This pair would totally work with dresses and skirts.
These are from A.P.C., and they’ve got a sophistication that I appreciate.
As regular readers know, I’m not especially fond of brown footwear, but I do very much like the burgundy-ish brown on this Frye pair.