New York streets put your shoes to the ultimate test. Not only do they physically test your shoes, but they also put the trend on trial. Yes, I’m talking about everything from the 2010 Jeffrey Campbell platforms (yes, everyone wore them all over Meatpacking) and the 2012 lace-up combat boots to the rise of the current sneaker trend; after living in New York for about a decade, odds are I’ve owned at least one pair of each trend. Through the transition of many apartments and countless closet clean-outs, there’s a sole shoe style (no pun intended) that has remained a constant in my closet.
My hero shoe style? The knee-high boot. Resting just below the kneecap, hugging the calves, and made with a minor slouch, these equestrian-inspired boots have yet to fail me. Though they’re currently having a major runway moment and beloved by celebrities including Kendall Jenner, Gigi Hadid, and Kaia Gerber, they’ve been around for quite some time. I have the latest pair from Ganni, but I also still have my first-ever pair from Stuart Weitzman from 2010.
With winter approaching and temperatures drastically dropping, your knee-high boots will come to the rescue. Layer them over thick tights under a skirt, or opt to go bare-legged with a cozy shearling coat; there are countless style options. Leather, suede, mock croc, and even plaid; indulge in the one shoe that will last you a lifetime. Scroll through our 20 favorites below.
You can’t go wrong with a little slouch.
Contrary to the heel height, these are very comfortable.
The founding father of knee-high boots.
Style trick: Match your boots to your coat.
’Tis the season of mock croc.
I need these. It’s not even a question.
A rare boot bargain.
Winter white is a thing.
You heard it here first—green is the color of the season.
You can never have too much snakeskin.
Try styling these in a navy monochromatic look.
This wider straight-leg silhouette is v. flattering.
Can’t forget an animal print option.
These are giving me The Row vibes.
Switch it up and opt for mix-matched boots.
These elegant boots will polish any outfit.
I’ll be wearing these throughout January and February (maybe even March).
I still get excited about the fact that Paige launched shoes.
Never knew I needed yellow boots until now.
At this price, these boots are going fast!
Bonus: These boots are waterproof, too.
Two words: yes please.
Another genius collab.
Up Next: I Plan to Only Buy 2 Pieces This Season, and Well, These Are Them
-
If Chic Jeans-and-Boots Outfits Are the Goal, Don't Miss These Standout Picks From Zara, Madewell, andReplica StoreBring on a stylish fall and winter closet.
-
My Honest Take on the Winter It Boots Every Fashion Person Is Talking AboutFrom Khaite to Free People.
-
Of All Her Outfits, *This* Hailey Bieber Look Is Stuck in My BrainAnd I will be re-creating it.
-
Just so You Know, Zara Already Has All the Best Shoes for Winter 2025Shop before they sell out.
-
Cool Sneakers, Flats, and Boots Are the Vibe—These 36 Styles Are Heavily Discounted for Black FridayEverything from Khaite to Ref to Adidas is at least 25% off.
-
If You're Going to Wear a Dress With Ankle Boots, This Is the Trend That Looks the Least DatedPSA via Suki Waterhouse.
-
Hilary Duff Knows the Smartest Boot Trend to Pair With Barrel JeansWhy didn't I think of this?
-
I Just Introduced My Best Friend to Everlane—Here Are the 31 Chic Black Friday Finds I Sent Her WayUp to 50% off rich-looking 2026 essentials.
