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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Whenever I'm in Paris, I See This Boot Trend Styled With Minidresses in Every Vintage Shop and Local BistroSorry, ankle boots, but it's not you.
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Everyone in Los Angeles Knows This Shoe Trend Makes Denim Shorts Look Way CoolerDenim shorts never looked so good.
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Spotted at Wimbledon: The Anti-Summer Shoe Trend You Don't Usually See in the StandsNever too hot for these.
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The $140 Boots London Fashion Girls Take Out of Storage Every Summer to Wear With Shorts and DressesFrom Kate Moss to Daisy Edgar-Jones.
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Stop With the Ankle Boots—Miniskirts Should Only Be Worn Like *This* in 2025Period.
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The Unexpected Shoe Style Fashion People Are Reaching For This SummerHere are seven ways to wear it.
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Oh, Hello! Meet the New It Ugg Boots You'll Spot on Fashion People and CelebsThese are about to be everywhere.
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Return Those New Flats—*These* Are the Cool Shoes Fashion People Are Wearing With Dresses and SkirtsFresh and unexpected.
