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.

These, from Vince, are so good in this sandy hue; however if that seems desperately impractical to you, they also come in black.

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.

The lovely Joy DaRos, who owns the Sullivan Street boutique JDR and Company—which is ground zero for all things Il Bisonte (and more)—gave me a gift card a while back, and it’s been burning a hole in my pocket. It took me a while to decide on a bag because so many of them are so good, but I finally went for this fabulous saddlebag in such a good blue. It’s just big enough for all the essentials, and the interior has three separate compartments, which is handy.

As I’ve mentioned here before, I’ve got a bad knee—torn meniscus, it turns out; surgery is imminent—and all I feel like wearing anywhere are sneakers. But most of mine don’t give me the height I crave. Most platform sneakers look too cartoonish and clunky to me, but these Vans come off reasonably proportional.

Have I shown you this Lee jumpsuit before? I honestly can’t recall. But it’s a good one, right?

And I like the hue—would we call it a dusty rose?—of this jumpsuit.

Cos calls this a  leather overshirt—which is like just a jacket, right?—and I think it’s nicely minimal and well-priced for what it is.

Surely I don’t need another puffer, but I might need this sherpa puffer from Madewell.

I’m also a fan of this Barbour puffer with great faux fur details.

I don’t typically love a high-neck sweater, but the high-V here is really quite good, and so is the moss brown color.

An oversized button down, the likes of which I’ve been living in these days, with light blue stripes.

I’ve got a silk V-neck top from Maria Cornejo that I wear endlessly, and which is definitely worse for wear. I’m thinking of replacing it with this crepe top, which is 100% polyester, but looks reasonably soft and breathable.

A cute half-zip pullover for throwing on whenever. And cheers to Madewell for continuing to employ models who weren’t born yesterday.

The frayed hem on and length of this denim skirt are both exactly perfect