Sarah Michelle Gellar & Freddie Prinze Jr.’s Best Early-2000s Fashion Moments

Steve Granitz/WireImage/Getty Images Fashion One of the best things to come out of the early aughts. by Maria Bobila Aug. 27, 2021

Yes, Sarah Michelle Gellar and Freddie Prinze Jr. are still together. The two first met on the set of I Know What You Did Last Summer in 1997, went on an impromptu first date three years later, and have been happily married since 2002. They’re any Y2K teen’s dream couple, and their memorable early-aughts wardrobe was the cherry on top of it all. Ahead, see Sarah Michelle Gellar and Freddie Prinze Jr.'s best couple fashion moments from the throwback era.

Steve Granitz/WireImage/Getty Images 2000, MTV Movie Awards The couple matching in leather-accented looks. Gellar won two MTV Movie Awards for Best Female Performance and Best Kiss (with Selma Blair) in Cruel Intentions.

George De Sota/Hulton Archive/Getty Images 2000, Boys and Girls Premiere Prinze wore a suit (sans tie) for the premiere of his movie Boys and Girls, while Gellar wore a sheer black blouse and trousers.

Albert L. Ortega/WireImage/Getty Images 2000, Teen Choice Awards The two took the simple route for the 2000 Teen Choice Awards: Gellar in gradient-tinted sunnies and a black midi dress, and Prinze in a tee and slacks.

KMazur/WireImage/Getty Images 2000, TNT’s Christmas in Washington Event Prinze, in a pinstripe suit, and Gellar, in a white low-back gown, wore their holiday best for TNT’s Christmas in Washington event in 2000.

Jim Smeal/Ron Galella Collection/Getty Images 2001, Golden Globes Gellar wore a printed Valentino halter gown with a matching sash, while (a blond) Prinze wore a black suit with a white tie.

Ron Galella, Ltd./Ron Galella Collection/Getty Images 2001, Teen Choice Awards The couple wore pastels for the 2001 Teen Choice Awards, with Prinze in a lavender dress shirt over a white tee and khakis, and Gellar in a mint one-shoulder top and jeans.

Mirek Towski/FilmMagic/Getty Images 2001, Summer Catch Premiere Prinze wore a slate gray dress shirt and black pants with square-toe (!) shoes to the premiere of his movie Summer Catch, while Gellar wore a lace-trimmed tank and pink pants.

Mirek Towski/FilmMagic/Getty Images 2002, Nickeloden Kids’ Choice Awards The two opted for jeans at the 2002 Nickelodeon Kids’ Choice Awards. Prinze paired his with a gray tee, while Gellar wore a statement top.

Steve Granitz/WireImage/Getty Images 2002, Scooby-Doo Premiere At the premiere of their movie Scooby-Doo in 2002, Gellar wore a white top-and-skirt set, while Prinze wore a brown dress shirt over a white tank and khakis.

Theo Wargo/WireImage/Getty Images 2002, MTV’s TRL The couple visited the set of MTV’s TRL. Prinze wore a black T-shirt with jeans, and Gellar wore jeans, as well, with a lace one-shoulder top.

James Devaney/WireImage/Getty Images 2002, SNL After Party Hitting up the SNL after-party in 2002, Prinze wore a white dress shirt and black pants, and Gellar wore a going-out tunic top with bootcut jeans, a brown jacket, and black hat.

Gregory Pace/FilmMagic/Getty Images 2003, New York Fashion Week Prinze and Gellar sat front row at Tommy Hilfiger’s Spring 2004 runway show. Gellar wore a string halter top and jeans, while Prinze wore a long-sleeve shirt and jeans.

Amanda Edwards/Getty Images Entertainment/Getty Images 2004, Scooby-Doo 2 Premiere On the red carpet for the premiere of Scooby-Doo 2 in 2004, Prinze switched things up in a cap and baby blue graphic tee with jeans, while Gellar wore a flowy blush pink top and white flare pants.

See more couple fashion throwback moments from Will and Jada Pinkett Smith in the ‘90s , Bennifer 1.0 , and early-aughts Beyoncé and Jay-Z .

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