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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Move Over, Jeans—The Chicest People I Know Are Wearing This Expensive-Looking Pant Trend With BootsSpotted on Naomi Watts.
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These Are the Surprising Shoe Trends Gen Z Is Styling With Everyday Outfits for the Rest of 2025Niche, weird, and unconventional.
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Forget Flats—Everyone With Good Taste Is Wearing These Boots With Jeans and a JacketPut these on your shopping list.
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Listen, Being Cool in 2025 Requires Just Two Things: Loose Jeans and This “Weird” Viral Flat-Shoe TrendThey're strange, but so chic.
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These Easy Outfit Formulas Make Even Fall's Most Polarizing Boot Trend Look CoolSee the inspiration inside.
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This Is the Luxe Fall Shoe Trend Every Fashion Person Is Already Wearing on RepeatCount these inspo pics as proof.
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It's Controversial (I Know), But Frequent Fashion Flyers Swear By This Jeans Outfit for Long FlightsIt involves an elegant leather coat and chic luggage.
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Taylor Swift Just Wore the Skirt-and-Boots Combo That Screams '90s Jennifer AnistonIt's foolproof.
