How It Girls Wore Ankle Boots in the '80s, '90s, and '00s
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.
Shop a similar style:
Shop a similar style:
Shop a similar style:
Shop a similar style:
Shop a similar style:
Shop a similar style:
Shop a similar style:
Shop a similar style:
Shop a similar style:
Shop more retro-inspired ankle boots:
Speaking of ankle boots, find out the best places to shop for the shoe staple and why.
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.
-
It's My Job to Find Wardrobe Staples, and These 35 Pairs of Black Boots Are ItWe're talking everything from sleek knee-highs to classic riding boots.
-
Here's the Comfy Yet Incredibly Chic Boot Style Fashion People Are Already Wearing on RepeatThese make any outfit look more expensive.
-
Irina Shayk and I Agree: Leggings Look Chicest With This Specific Boot Style and ColorTrust me.
-
Kaia Gerber Wore a Trench Coat Just Like a Parisian—With This '90s Skirt TrendA combination French girls love.
-
Not Skinny Jeans, Not Leggings—Everyone With Good Taste Is Wearing Boots With This Fall Staple InsteadThe chicest outfit formula of the season.
-
We Did the Research: These Are the 25 Best Pairs of Chelsea Boots, Hands DownThey're so back.
-
Meghan Markle and Kate Middleton Agree: This Boot Trend Is Made for Skinny JeansAre you on the same page?
-
Forget What You've Heard—Ankle Boots Are Still In, and This Expensive-Looking (But Just $50) Pair Is ProofGrab them before they're gone.

