Look Back at Britney Spears and Justin Timberlake's Iconic Matching Denim Moment

Few red carpet moments defined the fashion of an entire decade quite like Britney Spears and Justin Timberlake showing up to the American Music Awards in matching head-to-toe denim did for the 2000s. Between her Kurt and Bart patchwork gown paired with a rhinestone choker necklace and his light-wash Canadian tuxedo and denim cowboy hat ensemble, the pop stars and then-It-couple looked like a tacky Y2K dream.

To celebrate the iconic style moment — which inspired an era of mesh tops, tiny leather skirts, metallic frocks and (of course!) denim everything — we're looking back at how Spears and Timberlake's 2001 AMA looks came to be.

Speaking with Jezebel, the costume designer behind Timberlake's Canadian tuxedo, Steven Gerstein, opened up about bringing the look to life.

"It was such a no-brainer. Justin and Britney were dating at the time. We were in New Orleans when Britney and Justin were like, 'We're doing matching denim.' And I was like, 'How are you doing that? Who is doing that?' We wound up taking the Costume National suit that Justin wore for the Celebrity album cover. We remade it in denim. Conversations with Levi's were happening were happening at the same time, and Britney was working with Kurt and Bart. We had some crossover contacts at Levi's, so it went from being an idea to it being made within days."

"It was kind of like their prom. They had an idea, and we did what they wanted as opposed to the other way around," he continued. "The rest is history."

Timberlake reflected on the choice during an appearance on his former *NSYNC bandmate Lance Bass' The Daily Popcast in 2021 and admitted, "You do a lot of things when you're young and in love."

The "Cry Me a River" singer stood by his controversial look, "You can kind of rock that one today."

And Timberlake isn't the only one who still appreciates his special red carpet outfit — in fact, the denim-on-denim looks are so iconic that they have since become a high-ticketed auction item, a popular Halloween couple's costume and the inspiration behind many celebrity recreations.

Katy Perry and Riff Raff paid homage to Spears and Timberlake at the 2014 VMAs when they stepped out of a yellow Lamborghini in double-denim.

The key difference? While Spears and Timberlake were apparently completely earnest, Perry tweeted that her outfit was a custom Versace created for her due to her "love for nostalgia and … Tumblr addiction." From the patchwork denim pattern to the bedazzled choker, Perry nailed the Spears vibe, while Riff Raff captured Timberlake's essence with his goofy sunglasses and generally delighted demeanor.

Seemingly flattered, Spears gave Perry props for taking the look to the next level and bringing the denim gown out of retirement years later. "Just when I thought the denim dress had retired … you bring it back!" Spears tweeted to Perry at the time, "You looked amazing."