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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Everyone in Paris Just Ditched Ankle Boots for This Boot Style That's Way More ElegantAnd super sleek.
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*Not* Suede Boots: The Rich-Looking Boot Trend Fashion People Everywhere Are Wearing With Jeans and Skirts for Fall 2025You'll want to add a pair to your rotation.
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*Not* Ankle Boots—The Rich-Looking Shoe Trend That’s Quietly Taking Over for Fall 2025Shop the style inside.
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Laura Harrier Can't Stop Carrying This Timeless The Row Bag (and No, It's Not a Margaux)One, two, three times in one week.
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Black Boots Are Fine, But *This* Fall Shoe Color Trend Looks Rich as HellLily James is a fan.
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I Spent Over an Hour BrowsingReplica Store's New Arrivals—34 Standout Fall Finds I Can't Stop Thinking AboutYou'll want to see these.
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Not Skinny, Not Wide-Leg—J.Lo Just Wore Ankle Boots With 2025's Most-Wanted Pant TrendCopy this fall outfit ASAP.
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Calvin Klein's '90s Collections Will Always Be My Blueprint for Fall DressingFall 1994 especially.
