The Chic Ankle Boot Style That Goes With Everything
For most of us, winter means trudging through snow and ice in our sturdiest winter boots. However, as practical as those may be, they aren’t always the most stylish. We’re not ones to sacrifice our safety for style, but in those moments when you aren’t trekking from place to place, give yourself a boost—literally and figuratively—with a pair of stiletto ankle boots.
As tempting as it may be to reach for your block heels or combat boots this season, sleek stiletto booties will give your ensemble an unparalleled level of chic. Whether you dress up a casual sweater with jeans or amp up a sophisticated office look, this ankle boot style is guaranteed to go with anything you wear (we promise!). Ahead, check out some of our favorite versions of this classic ankle boot style.
You’ll look so good wearing these everywhere.

-
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?
-
It's Official: These Are *the* It-Girl Uggs of Winter 2025Selena Gomez just solidified it.
-
I'm a Shopping Editor—These Are the Cool Shoes I Care About From theReplica Store Black Friday SaleTake up to 60% off 2025 shoe trends inside.

