How It Girls Wore Ankle Boots in the '80s, '90s, and '00s

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(Image credit: Getty Images)

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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Paulina Porizkova in 1985
(Image credit: Arthur Elgort/Condé Nast/Getty Images)

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Halle Berry in 1994
(Image credit: Ron Galella, Ltd./Getty Images)

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Gwyneth Paltrow in 2001
(Image credit: Jim Spellman/Getty Images)

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Naomi Campbell in 1998
(Image credit: RON GALELLA, LTD./WIREIMAGE )

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Anna Wintour in 2004
(Image credit: Stephen Lovekin/Getty Images)

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Jennifer Aniston in 1998
(Image credit: Ron Galella Ltd./WireImage)

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Julia Roberts in 2001
(Image credit: Getty Images)

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Victoria Beckham in 2000
(Image credit: Justin Goff/Getty Images)

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Sarah Jessica Parker in 2003
(Image credit: Mario Magnani/Getty Images)

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Speaking of ankle boots, find out the best places to shop for the shoe staple and why.

Senior Editor

Anna is an NYC-based senior fashion editor who has been a member of the Who What Wear team for over seven years, having begun her career in L.A. at brands like Michael Kors and A.L.C. As an editor, she has earned a reputation for her coverage of breaking trends, emerging brands, luxury shopping curations, fashion features, and more. Anna has penned a number Who What Wear cover interviews, including Megan Fox, Julia Garner, and Lilly Collins. She also leads the site’s emerging travel vertical that highlights all things travel and lifestyle through a fashion-person lens.