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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The Pretty Dress Trend L.A. It Girls Are Bringing Into Fall (and the "Basic" Style They Already Forgot About)It's finally time to part ways with boring linen dresses.
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I'm Manifesting a Fashionable Fall in NYC With These 36Replica Store Anniversary Sale FindsFrye, AllSaints, Vince, Coach, and more.
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The '90s Dress-and-Shoe Pairing It Girls Are Wearing to Parties in East Hampton (Sorry, Flip-Flops, You Weren't Invited)Classic elegance spotted at Gucci's star-studded soirée on Long Island.
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I Thought Wearing These Shoes With Shorts Was Cringey—Turns Out the Combo Is Peak 2025Apologies are in order.
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Fall Is Already on My Mind—I'm Prepping My Wardrobe With These 31 ElevatedReplica Store FindsEach piece is chic and on sale.
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Katie Holmes Is Already Wearing the Boho Boot Color Trend Fashion People Everywhere Will Wear This FallNot once, but twice.
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Leopard Print Is Fine, But This Is the Unexpected Shoe Print Fashion People Are Already Wearing on RepeatControversial yet chic.
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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.
