Great Outfits in Fashion History: Anna Kournikova’s Y2K Denim-Print Dior Dress

There are perfectly good celebrity style moments, and then there are the looks that really stick with you, the ones you try desperately to recreate at home. In ‘Great Outfits in Fashion History,’ Fashionista editors are revisiting their all-time favorite lewks.

I didn’t grow up playing tennis, and if I’m honest, I still don’t find the sport particularly entertaining. But it’d be a lie to say I haven’t fallen down the #tenniscore rabbit hole like every other algorithm-driven fashion girlie. (The pleated skirts and knit polos caught my interest, but Zendaya’s “Challengers” press run is what had me sold. Law Roach, you did your big one with that.)

Because it’s in my genes to show anything but self-restraint, my tennis-inspired sartorial fascination continued all the way to exploring ’90s and early-2000s fashion archives. It’s what led me to a standout look by (then) tennis star and Russian model Anna Kournikova.