Why Fiona Apple Is the Style Icon We Need Right Now

If there’s one trait that defines a Fiona Apple fan, it’s patience. A notorious perfectionist, the singer is happy to spend the better part of a decade fine-tuning an album; thankfully, the result is always worth the wait. Operating outside of the industry cycle, every one of her records offers a window into the world of a musician who keeps her personal life fiercely protected, only to return seemingly out of nowhere with music so bracingly candid that it more than fills in the gaps.

So, quite what she’s been up to since the release of her most recent record, 2012’s The Idler Wheel…has remained a mystery. That is, until she was thrust back into the pop-cultural consciousness this month, thanks to a Jennifer Lopez striptease sequence in the star’s latest (and heavily Oscar-tipped) film, Hustlers. J.Lo’s mesmerizing opening performance sees her spinning around a pole in a downtown Manhattan strip club, as sleazy Wall Street types chuck money at her—the most gloriously campy introduction to a character since Liza Minnelli stepped onstage wearing a bowler hat in Cabaret, or Gina Gershon performed her first dance in Showgirls.

And, in an inspired choice, soundtracking it all was Apple’s 1997 hit “Criminal,” released when the singer was 20. Like all of the music in Hustlers, it perfectly reflects the film’s faithfulness to its ‘00s zeitgeist—but the inclusion of “Criminal” in 2019 feels particularly apt, as Apple’s laid-back, irreverent style undergoes something of a renaissance among a new generation of female musicians. In predictably unpredictable form, Apple cold-emailed a journalist earlier this week who had tweeted about a controversial video that overlooked her donations of the royalties from Hustlers to a charity supporting refugees; the conversation ended up taking the form of an accidentally sprawling interview—her first in seven years—with plenty of Apple’s forthright sense of humor, and the news that a record is likely to arrive next year.

Thankfully, the time is ripe for a Fiona Apple style revival. The singer’s signatures aren’t defined by any specific item of clothing, but a don’t-give-a-fuck attitude that feels totally of the moment—an outlook best summarized by her divisive speech when accepting the award for Best New Artist in a Video at the 1997 VMAs for her single “Sleep to Dream,” where she memorably described the assembled members of the music industry’s world as “bullshit.” Her favored look at the time was a grunge-inspired ensemble of a cropped tank top and a pair of baggy trousers, or occasionally a silk slip dress, her hair left to curl up at the ends with pointedly minimal effort.

It’s an iconoclastic, easy-going spirit that has been adopted by many of Apple’s young acolytes working in the world of pop today: Just take Billie Eilish’s super-comfy tour wardrobe of tracksuits and oversize separates, or Charli XCX’s easy, breezy, ‘90s-inspired spaghetti-strap boob-tubes and miniskirts. Even King Princess, who can now boast Apple as a friend after locking her down for a collaborative cover of the 1999 track “I Know,” has channeled the singer’s chic androgyny with her casual take on menswear staples. There might have been precedents, but Apple’s insistence on putting her music ahead of crafting a fashion-adjacent image made her an accidental pioneer, and a new crop of pop musicians now understand clothing as one of many tools within their stable, rather than something that defines them.

But then—in keeping with her sprawling sartorial tastes—it isn’t any specific garment, or any particular look that makes Fiona Apple’s very casual style feel perfectly right for now. It’s the fact that clothes have always been a key device when telling her story, even if they were never the opening gambit; and with the low-key role they’ve played in her career, her humble take on fashion has been criminally (pun intended) overlooked. Apple’s return to music next year can’t come quickly enough—but while we’re at it, maybe it’s time to reassess the ongoing influence of her off-kilter style, too.

Originally Appeared on Vogue