Britney Spears and Justin Timberlake

Britney Spears Dishes On Her 'Tacky' Matching Denim Outfit With Justin Timberlake

Home / Fashion / Britney Spears Dishes On Her 'Tacky' Matching Denim Outfit With Justin Timberlake

By Kristin Myers on October 24, 2023 at 6:15 PM EDT

Pop star Britney Spears has shared a lot of details about her ex-boyfriend, Justin Timberlake, in her memoir, "The Woman In Me."

Although the 41-year-old pop star gets candid about allegations of infidelity and an unplanned pregnancy that rocked the relationship, she also touches on some lighthearted topics, such as their "tacky" matching denim outfits.

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Britney Spears Reflects On Her and Justin Timberlake's 'Tacky' Matching Denim Outfit

In an excerpt of "The Woman In Me" shared by People magazine, Britney reflected on the time that she and Justin wore matching denim outfits to the 2001 American Music Awards.

In her memoir, she explained that the decision to twin in denim was partially inspired by her upbringing in the South, where "moms love to round up the kids and say, 'Listen, we're going to church today, so we're all going to color-coordinate.'"

When she found out that the "Cry Me A River" singer was planning to wear denim to the awards show, she said, "We should match! Let's do denim-on denim!"

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That being said, the "Oops!... I Did It Again" singer said that she only meant it as a joke and didn't expect him to like her idea. "At first, honestly, I thought it was a joke," she recalled. "I didn't think my stylist was going to do it, and I never thought Justin was going to do it with me. But they both went all in."

She said that stylist Steven Gerstein assembled a "Canadian tuxedo" outfit for the "Mirrors" crooner, prompting Britney to reflect, "When he put it on, I thought, 'Whoa! I guess we're really doing this!'"

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Although the "Womanizer" singer recalled how they had often color-coordinated outfits as a couple, she said, "But with the matching denim, we blew it up." She recalled how "My corset had me sucked in so tight under my denim gown, I was about to fall over" and now understands why so many mocked the look over the years.

"I get that it was tacky — but it was also pretty great in its own way, and I'm also happy to see it parodied as a Halloween costume," she wrote, confessing, "I've heard Justin get flak for the look."

"On one podcast where they were teasing him about it, he said, 'You do a lot of things when you're young and in love,'" she continued. "And that's exactly right. We were giddy, and those outfits reflected that."

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Fashion Stylist Steven Gerstein Weighs In The Fashion Statement

Justin Timberlake And Britney Spears
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In 2020, ahead of the 20th anniversary of their AMAs fashion statement, Steven Gerstein reflected on the look to Jezebel, saying, "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," Gerstein recalled. "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," Gerstein added. "They had an idea, and we did what they wanted as opposed to the other way around. The rest is history."

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"The Social Network" actor also reflected on the look in 2020 when he appeared on Lnce Bass' podcast. He doubled down on his look to his NSYNC bandmate, saying, "You can kind of rock that one day" before he went on to confess, "You do a lot of things when you’re young and in love."

As People magazine noted, many celebrities have replicated the look this year. At the 2014 MTV Video Music Awards, "I Kissed A Girl" singer Katy Perry wore double-denim when she walked the red carpet with red carpet. At the time, the "Roar" singer tweeted that her custom Versace outfit was inspired by her "love for nostalgia and … Tumblr addiction."

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Britney acknowledged the look on Twitter, responding, "Just when I thought the denim dress had retired … you bring it back!"

It remains to be seen how many fans will be wearing denim for Halloween!

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