A Look Back at Fiona Apple’s Peak ’90s Style

If you haven’t yet listened to the masterpiece that is Fetch the Bolt Cutters, Fiona Apple’s fifth studio album, close this tab and get to it. If you have, you’re likely longing for the days when the reclusive singer was everywhere. Luckily, there exists a time capsule of sorts. Apple’s style was so thoroughly ’90s that photos from the Tidal and When the Pawn… era vividly capture the decade. Her wardrobe essentials were a ’90s checklist, featuring clogs, spaghetti straps, flare jeans, and crimped hair. When performing, she took care to showcase her belly button piercing; if she wasn’t already wearing a crop top, she’d fashion one herself by tying up her shirt. But on the red carpet, Apple often stuck to tradition—at least, when it came to events like the Oscars. There was nothing conventional about the ensemble—not to mention sparkly yellow makeup—she wore to the VH1 Fashion Awards in 1997. Here, revisit those looks and more, like the surprisingly simple one on the infamous night she took the stage of the VMAs and declared “the world is bullshit.”