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.
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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.
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If a French Woman Shopped the Gap and Banana Republic Sales, These 30 Chic Picks Would Catch Her EyeOui, merci!
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It's Official: French Women Love This Boot Style for SpringHere's how they are styling it.
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When Sydney Sweeney and Lady Gaga Own the Exact Same Boots, You Know They're GoodGreat minds think alike.
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I Want to Build a New Wardrobe—30 Incredibly Elegant Pieces I'm Eyeing From the Nordstrom Winter SaleBring on the chic outfits.
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I Forgot About These Winter Boots Until Meghan Markle Styled a Pair In the Most 2025 WayGood thing they're on sale.
