There's no shortage of outfit inspiration from decades past, whether it's the bright colors, puffy sleeves, and graphic prints of the '80s that are currently trending again or the minimalistic all-black ensembles of the '90s that have become our forever mood at this point. Since we're always looking to the past, there's rarely a moment where we're not channeling the nostalgic outfits from one (or all) of these iconic moments in fashion history. Since ankle boot season is nearly upon us, we took a deep dive into photo archives from these decades, and we're happy to report that we found a trove of cool outfits with ankle boots.
After seeing the following outfits from It girls like Halle Berry, Naomi Campbell, and Gwyneth Paltrow, you'll realize that so many of the It trends they were wearing with their ankle boots are eerily similar to today's trends (think leopard-print, croc-effect, and square-toe shoes). If you're craving some throwback style inspiration, look no further. These cool outfits will have you instantly craving cooler weather so you can finally break out all the faux fur, leather, and chunky knits just begging to be styled with a classic pair of ankle boots.
Shop a similar style:
Shop a similar style:
Shop a similar style:
Shop a similar style:
Shop a similar style:
Shop a similar style:
Shop a similar style:
Shop a similar style:
Shop a similar style:
Shop more retro-inspired ankle boots:
This quirky zipper deserves another look.
By Far's sleek boots are a fashion-girl favorite.
Yes, you need another pair of white ankle boots.
This color feels so fresh.
Céline vibes.
Speaking of ankle boots, find out the best places to shop for the shoe staple and why.
-
I Walk Over 5 Miles A Day Working in Manhattan—Here’s an Editor-Approved City Girl’s Guide To Fall ShoesPlus, how I'd style them.
-
Forget What You've Heard—Ankle Boots Are Still In, and This Expensive-Looking (But Just $50) Pair Is ProofGrab them before they're gone.
-
Wearing a Preppy Cardigan With This Controversial Boot Trend Makes It Look 10x CoolerYou won't believe it.
-
I'm Building the Boho-Chic Closet of My Dreams—31 Fall Finds From Free People and Anthropologie That Fit the BillLet's talk about micro shorts and Western boots.
-
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.
