24 Boots You’ll Want to Wear this Winter

24 Boots You’ll Want to Wear this Winter

If that’s not clickbait, we don’t know what is.

Well, it’s been a good run, fall. What was it this time—like, five days?

Halloween is over, and before we knew it, bang (or you know, boo)—the pumpkins are smashed, Harry Connick Jr. is crooning about sleigh rides over mall speakers, and the degrees are dropping below 32 faster than a socialite asked her age.

Ah, early November. Official sponsor of “too soon.”

So you’ll forgive us when we admit to seeking seasonal-affective consolation in leather, suede, lace-ups and lug soles. In our defense, northerly climates don’t exactly lend themselves to just-one-pair winters—so stocking up on boots of all shapes, heights and degrees of walkability is basically a survival tactic.

In the immortal words of Regina George: Get in, losers, we’re going shopping.


Perfect for snowless occasions—or stubborn “no, my feet are NOT cold” retorts—the ankle boot toes the line (sorry) between functional fall attire and those salt-encrusted, barely recognizable footwear-formerly-known-as-boots you refuse to take off come mid-December because they go with literally everything and are the most comfortable things you own. Our tried-and-true* solution: Buy a lot of them, put them on steady rotation ‘til March and hope you don’t get frostbite.

*Not tried and probably false.


We’d describe these as a little more practical than ankle boots, but still far from Mom-approved winter gear. So in essence, they’re perfect. Suki Waterhouse and Rosie Huntington-Whiteley are fans, so we can therefore deduce this style pairs well with supermodel status. We’re opting for a well-rounded supply of heeled, combat, rain and cowboy, just to cover our boot-bases.


Perhaps the sleekest of the boot brigade, these tall orders are a trend-transcendent standard in our closets (which also happen to be super trendy this season—see: Saint Laurent). This year’s contingent of slouchy riding boots, asymmetrical edges, platform soles and oh-so-practical cutouts have us weak in the knee-highs. Because, to echo (with creative liberties) Iggy Azalea in this year’s lyrical masterpiece, “Booty”, the last time we seen boots this good, they were on Jenny from the Block.

—Chelsey Burnside
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