The Britney Spears Fashion Flop That Became One Of Her Most Iconic Looks

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Britney Spears made history when she and Justin Timberlake showed up at the 2001 AMAs in matching denim-on-denim ensembles that would become of one of the most referenced red carpet looks of that era. You know the one. The look has been recreated and reimagined 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. Clad in a strapless patchwork dress by the fashion duo Kurt and Bart, Spears accessorized her outfit with a rhinestone choker necklace, a denim purse, 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 to Jezebel, recalling how the looks came together almost 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 were like, 'We're doing matching denim.' And I was like, 'How are you doing that? Who is doing that?'" said the designer. But it was settled: they decided to take a suit Timberlake had worn on the cover of NSYNC's "Celebrity" album and turn it into a Canadian tuxedo. 

They never thought the matching looks would end up becoming a pop culture moment. "[I]t was just two kids, wanting to do something cool, and being 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."

Twenty-two years after their infamous double denim ensemble, Britney Spears revisited the fashion moment in her tell-all memoir, "The Woman in Me," while reminiscing about her relationship with Justin Timberlake. She recalled pitching the idea to her stylist and Timberlake after learning that he intended to wear an all-denim look to the 2001 AMAs. But she was mostly joking. "I didn't think my stylist was actually going to do it, and I never thought Justin was going to do it with me," wrote Spears (via People). To her surprise, however, "[T]hey both went all in." At the time, she and Timberlake had been dating for over two years and were actively going to events together. "We often color-coordinated our outfits," Spears remembered. "But with the matching denim, we blew it up."

Looking back, the '90s icon admitted the denim outfits were cheesy and over the top, but overall, she doesn't mind it. Spears said seeing the look being recreated and parodied never fails to bring a smile to her face. She also agreed with Timberlake's remark that those are the kinds of choices you make when you're madly in love. (They ultimately broke up in 2002, just one year after this red-carpet appearance.) "And that's exactly right," Spears echoed. "We were giddy, and those outfits reflected that."

As for Timberlake, he considers the matching looks awful and would gladly erase it from memory if he had the chance. He mentioned the outfits in a Playboy interview while lamenting on some of his fashion choices. "Yeah, [that was a] bad choice," he said of the look. "God, I feel I've gone to therapy just to erase some of them [...] I'd probably pay good money to get some of those pictures off the internet," he added (via GQ).