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.

-
Jeans, Who? It Girls Everywhere Are Wearing Boots With This Anti-Denim Trend Right NowIt will also be a fashion person's go-to uniform this winter, too.
-
This "Ugly" Shoe Trend Is Officially Back From 2016—But This Time, It's BetterSpotted in London and NYC.
-
This Is the 2025 Way to Wear the Ankle Boot Trend Everyone Bought 4 Years AgoPSA: Don't toss them yet!
-
Move Over, Jeans—The Chicest People I Know Are Wearing This Expensive-Looking Pant Trend With BootsSpotted on Naomi Watts.
-
These Are the Surprising Shoe Trends Gen Z Is Styling With Everyday Outfits for the Rest of 2025Niche, weird, and unconventional.
-
Forget Flats—Everyone With Good Taste Is Wearing These Boots With Jeans and a JacketPut these on your shopping list.
-
Listen, Being Cool in 2025 Requires Just Two Things: Loose Jeans and This “Weird” Viral Flat-Shoe TrendThey're strange, but so chic.
-
These Easy Outfit Formulas Make Even Fall's Most Polarizing Boot Trend Look CoolSee the inspiration inside.

