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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My Honest Take on the Winter It Boots Every Fashion Person Is Talking AboutFrom Khaite to Free People.
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Of All Her Outfits, *This* Hailey Bieber Look Is Stuck in My BrainAnd I will be re-creating it.
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Just so You Know, Zara Already Has All the Best Shoes for Winter 2025Shop before they sell out.
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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.
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If You're Going to Wear a Dress With Ankle Boots, This Is the Trend That Looks the Least DatedPSA via Suki Waterhouse.
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Hilary Duff Knows the Smartest Boot Trend to Pair With Barrel JeansWhy didn't I think of this?
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It's Official: These Are *the* It-Girl Uggs of Winter 2025Selena Gomez just solidified it.
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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.
