Admit it: fashion isn’t the first thing that comes to mind when you think of Britney Spears. The millennial pop icon has worn her fair share of statement looks—who can forget the his and hers denim outfits she wore at the 2001 American Music Awards with then-boyfriend, Justin Timberlake—but despite being a Vogue cover star, Spears’s style has often been overshadowed by her personal life.
The star, who turns 38 today, has led a tumultuous life in the public eye, but has also emerged as one of pop music’s greatest survivors. For nearly three decades she’s given the world upbeat hits, jaw-dropping music videos, and plenty of striking red carpet moments.
Currently a fan of sparkly Saint Laurent mini dresses and showgirl-worthy designs from Zuhair Murad, Spears’s fashion prowess was most evident in the early-aughts. At the height of her powers—and with access to the best of everything—she indulged in many of the decade’s biggest casual trends (flared jeans and Juicy Couture tracksuits, anyone?) but always dressed up when the event called for it.
Whether that meant a sparkly Stella McCartney-era Chloé jumpsuit at the 2000 American Music Awards, or rainbow sequined Versace to pose backstage with Donatella at the brand’s Spring 2003 collection, she regularly dipped her toes into designer fare. Though she never aspired to become a front-row fixture or set trends, a look back at Spears’ greatest fashion hits proves she managed to make an impact all the same.