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Britney Spears made history when she and Justin Timberlake appeared at the 2001 AMAs in matching denim-on-denim ensembles that would become one of the most talked about red carpet looks of the era. You know the one. The look has been recreated and recreated by dozens of celebrities (perhaps most famously by Katy Perry and Riff Raff at the 2014 VMAs) and fans (often as a Halloween costume), but at the time it was considered a fashion flop. Wearing a strapless patchwork dress by fashion duo Kurt and Bart, Spears accessorized her outfit with a rhinestone choker necklace, a denim clutch and a silver belt. Meanwhile, Timberlake sported a custom denim suit by Steven Gerstein, complete with a matching hat, boots and sunglasses.
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In honor of the fashion moment, Gerstein spoke Jezebelrecalling how the look came together nearly two decades after the so-called “Prince and Princess of Pop” made a splash on the AMAs red carpet. “We were in New Orleans when Britney and Justin said, ‘We’re doing matching denim.’ And I was like, ‘How do you do that? Who does that?'” the designer said. But it was settled: they decided to take a suit that Timberlake had worn on the cover of NSYNC’s “Celebrity” album and turn it into a Canadian tuxedo.
They never thought the matching look would end up being a pop culture moment. “(I)t was just two kids who wanted to do something cool and be super cute, matching,” Gerstein told the outlet. “It was kind of like their prom.” He added: They had an idea and we did what they wanted, as opposed to the other way around. … The rest is history.”
Britney Spears Admits Her 2001 AMAs Look Was ‘Tacky’
Twenty-two years after their infamous double denim ensemble, Britney Spears revisited the fashion moment in her all-encompassing memoir, “The Woman in Me,” while reminiscing her relationship with Justin Timberlake. She recalled pitching the idea to her stylist and Timberlake after learning he intended to wear an all-denim look to the 2001 AMAs. But she was mostly joking. “I didn’t think my stylist would actually do it and I never thought Justin would do it with me,” Spears wrote (via People). To her surprise, however, “(T)hey both went all in.” At that time, she and Timberlake had been dating for over two years and actively went to events together. “We often color-coordinated our outfits,” Spears recalled. “But with the matching denim, we blew it up.”
Looking back, the ’90s icon admitted the denim outfit was cheesy and over the top, but overall, she doesn’t mind. Spears said seeing the look recreated and parodied never fails to bring a smile to her face. She also agreed with Timberlake’s remark that these are the kinds of choices you make when you’re madly in love. (They eventually broke up in 2002just a year after this red carpet.) “And that’s absolutely true,” echoed Spears. “We were giddy and those outfits reflected that.”
As for Timberlake, he thinks the matchup looks terrible and would gladly erase it from his memory if he had the chance. He mentioned the outfit in a Playboy interview while lamenting some of his fashion choices. “Yeah, (it was a) bad choice,” he said of the look. “God, I feel like I’ve gone to therapy just to delete some of them (…) I’d probably pay good money to get some of those pictures off the internet,” he added (via GQ).
