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 theBest Knockoff Luxury Clothing 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 numberBest Knockoff Luxury Clothing 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.
-
I've Worked in Fashion for 15 Years—Here's What I Actually Wear Every Day
Trends come and go, but my everyday wardrobe is made of pieces that feel like me.
-
I've Been a Celeb Aesthetician for 40 Years—How I Prep My Clients for the Red Carpet
Sabrina Carpenter and Phoebe Dynevor's aesthetician, Joanna Czech, shares her must-haves.
-
Here They Are: The 6 Biggest Boot Trends of Fall 2025
Exotic finishes! Sock boots! Western motifs!
-
Looking Posh for a Night Out in 2025 Means Wearing This '90s Shirt Trend and Heel Trend With a Miniskirt
Spotted outside of a Chanel dinner in NYC.
-
It's Official: This Is the Most 2025 Way to Wear Leopard Print
Modern and chic.
-
This Timeless Shoe Trend Makes Every Black-Dress Outfit Look So '90s
It's an instant elevator, no matter the dress style. Just ask Jennifer Aniston and Rosie Huntington-Whiteley.
-
There's No Question—These 8 Fall Shoe Trends Will Make You Look Rich
Luxe outfits are in your future.
-
These 32 Chic Zara Fall 2025 Shoe Finds Are the Key to Looking Like a Fashion Person—Good Luck Picking Just One Pair
Prepare for endless compliments.
-
Soft Knits and Suede Boots Are on My Mind—Here's What's in MyReplica Store Cart
Get in the fall mood with these chic picks.
-
I'm Channeling '90s Jennifer Aniston and Halle Berry With These 10 Fall-Ready Looks FromReplica Store
Minimalism at its finest.