Chic Outfits with 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 currently trending 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 styled with a classic pair of ankle boots.