When Y2K fashion made its triumphant return a few years ago, I had my reservations, but like most other people, I softened over time to a few of the era’s trends. Case in point: clear PVC shoes. Brands like Maryam Nassir Zadeh, Amina Muaddi, and Magda Butrym brought wedge versions into the 2020s, breathing new life and interest into the long-outdated footwear style. As trends do, though, Y2K peaked and fell, and by now, most trends from the time have lost favor.

As for clear shoes, I was ready to ditch my pairs forever. In fact, up until a few hours ago, they were in a donation bag in my living room waiting to be picked up. It wasn’t until I saw photos of Olivia Rodrigo’s appearance on The Tonight Show Starring Jimmy Fallon last night that I began to think twice about giving the trend up for good.

Singer-songwriter Olivia Rodrigo arrives on Tuesday, October 29, 2024 wearing a red Ludovic de Saint Sernin chainlink minidress with clear wedges.

(Image credit: Todd Owyoung/NBC via Getty Images)

On Olivia Rodrigo: Ludovic de Saint Sernin dress; Amina Muaddi Lupita Glass Wedge Sandals ($1105)

For the episode, Rodrigo chose a red minidress from Ludovic de Saint Sernin’s S/S 25 collection (similar to the ones Laura Harrier and Ella Hunt wore at the 2024 Academy Museum Gala a few weeks ago) and a pair of clear PVC wedge sandals from Amina Muaddi. The combination just made sense, and with one look, Rodrigo’s controversial heel choice began to feel timeless and classic rather than trendy.

Kim Kardashian at the Fourth Annual Academy Museum Gala held at Academy Museum of Motion Pictures on October 19, 2024 in Los Angeles, California.

(Image credit: Gilbert Flores/WWD via Getty Images)

On Kim Kardashian: vintage Mugler couture one-piece and coat; Tiffany & Co. jewelry