Long Live Anastacia’s Y2K Style

Last weekend, while en route to my friend David’s birthday party at a karaoke bar, we decided to blast 2000s hits in the Uber for inspiration. Anastacia’s “I’m Out Love” reverberated via the auxiliary chord. “She is so underrated,” I exclaimed as the soulful singer crooned, “I’m outta love, set me free—and let me out this misery!” Equally as underrated, I thought, is Anastacia’s Y2K style. When her third studio album, Anastacia, dropped 20 years ago, there were few pop stars nailing the early-aughts aesthetic quite like she did. So let’s revisit it, shall we?

Sure, you may think of household names like Britney Spears or Destiny’s Child when recalling Y2K style, but I’d argue Anastacia was another key player in defining the look of the time period. When you think of 2000s pieces, low-rise jeans, big faux fur coats, Bermuda shorts, crop tops, and colorful shield shades likely come to mind. These are all pieces that Anastacia was wearing on the red carpet at the time, helping to shape a whole fashion aesthetic that some argued was tacky, but refreshingly leaned on playfulness and not taking oneself too seriously.

Photo: Getty Images

These days, of course, fashion has mostly moved on from the gaudy 2000s in favor of stealth-wealth and minimalism (though last year saw both the runways and celebrities revive the flashy Y2K aesthetic). Yet, even if it's now considered retro, there was something really interesting about the way that Anastacia was putting outfits together during the decade. At the Latin American VMAs in 2002, for instance, she hit the red carpet in a striped crop top with a brown leather skirt and red tinted aviators. While attending the premiere of Fahrenheit 9/11 in 2004, Anastacia stepped out wearing a sleek navy leather trench coat with a sheer, Botticelli-print dress by Dolce & Gabbana. Plus, accessorized with the buckled wedge sandals? Cute.

The looks were full of attitude and spontaneity. Her approach to fashion was fun, and reflected a time when celebrities didn’t have huge glam teams or stylists—they simply wore what they liked, and ran with it. And even 20 years later, both her album (please listen to Left Outside Alone) and her outfits still hold up. Sure, maybe you’d dial things back a bit in 2024—maybe forgo the hat, sunglasses, and statement earrings all at once—but pick a few elements from Anastacia’s early aughts outfits, and you still have a winning look today. She’s, quite simply, the underrated queen of Y2K style.

Below, more of her best Y2K outfits.