In her new memoir, 'The Woman in Me,' Spears looks back on the iconic fashion moment when she and Timberlake wore matching denim outfits to the 2001 American Music Awards
Back when she and the former *NSYNC star were dating, the pair famously showed up to the 2001 American Music Awards in matching head-to-toe denim looks. Now, more then 20 years later, Spears, 41, is admitting that the fashion statement was "tacky."
She opened up about the memorable outfits in her new memoir, The Woman in Me, released on Tuesday, saying the decision to double up on denim was partly 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 Timberlake was planning to wear denim to the awards show, she suggested to him, "We should match! Let's do denim-on-denim!"
However, she wasn't actually serious. "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."
For Timberlake, stylist Steven Gerstein assembled a version of a "Canadian tuxedo" with a denim jacket, pants, shirt and — to top it off — a western-inspired hat complete with a button waistband detail.
"When he put it on, I thought, 'Whoa! I guess we're really doing this!'" wrote Spears, who donned a strapless floor-length patchwork denim dress and carried a small denim bag at the event.
It was hardly the first time the duo had done matching looks. Spears said they enjoyed stepping out together in color-coordinated outfits when they were a couple from 1999 to 2002. "But with the matching denim, we blew it up," she said of the over-the-top AMAs ensembles.
She also remembered suffering for the sake of fashion that night. "My corset had me sucked in so tight under my denim gown, I was about to fall over," she explained.
As she looks back on the outfits now, she understands why they've been so widely roasted 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.
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Spears acknowledged that Timberlake has also endured plenty of ribbing for his part in the Y2K denim disaster.
"I've heard Justin get flak for the look," she wrote.
"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."
In 2020, ahead of the 20th anniversary of the AMAs fashion statement, Gerstein explained how Timberlake's look came 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?'" he recounted to Jezebel.
"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 [costume designers] 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," Gerstein added. "They had an idea, and we did what they wanted as opposed to the other way around. The rest is history."
“You can kind of rock that one today,” Timberlake told Bass of the denim-on-denim trend, adding, "You do a lot of things when you’re young and in love."
In addition to becoming an enduringly popular couple's Halloween costume theme, Spears and Timberlake's denim looks have also been recreated by numerous celebrities through the years, including Katy Perry. She and Riff Raff walked the red carpet at the 2014 VMAs in double-denim, treating fans to a fun fashion flashback.
At the time, Perry, 38, tweeted that her custom Versace outfit was inspired by her "love for nostalgia and … Tumblr addiction."
Spears acknowledged the recreation, tweeting Perry at the time, "Just when I thought the denim dress had retired … you bring it back!"
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