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.
-
Wearing Cropped Jeans With This Type of Shoe Keeps Them From Looking DatedYou probably already own them.
-
I Want a Rich-Looking Wardrobe—33 Perfect Picks FromReplica Store's (Early) Black Friday SaleGet a head start with these chic gems.
-
8 Nineties Winter Trends That Are on the Verge of Going ViralIs it 1994 or 2024?
-
Pleated Pants Are Everywhere, But Bella Hadid Just Swapped Them for a Fresh '90s Trouser TrendI might have to copy her.
-
Katie Holmes Made This Outdated Leggings-and-Boots Outfit Feel Just Right for 2025A combo I will live in.
-
J.Lo Wore the Brand-New Uggs That'll Go Viral and Sell Out By December 1—GuaranteedDon't say I didn't warn you.
-
Zoë Kravitz Just Wore the One Winter Boot Trend That Every Chic Celeb Agrees OnDakota Johnson and Sofia Richie are also fans.
-
Katie Holmes Just Wore the Elegant Boot Color New Yorkers Are Abandoning Black ForTake note.
