Britney Spears and Justin Timberlake are back. No, it’s not 2001, but it certainly feels like it. Spears recently released a previously unreleased song she cowrote with Timberlake, titled “She’ll Never Be Me,” which was originally recorded for Spears’ 2001 album “Britney.” Ahead of the 25th anniversary edition of the album, out Nov. 6, WWD is looking back at the style moments that defined Spears’ and Timberlake’s relationship.
While Spears and Timberlake began dating sometime in 1999, the former couple’s most famous — or infamous, depending on one’s perspective of the fashion choice — style moment was their double-denim designs worn to the 28th American Music Awards in January 2001.
Spears’ custom denim dress was designed by Kurt and Bart, featuring a formfitting silhouette and flowing skirt with a train. A loose hip belt, stacked sparkling bracelets and statement necklace, along with a denim purse, added a bevy of glitter to the look.
The matching moment was made complete with Timberlake’s denim suit and coordinated hat, which was designed by Steven Gerstein in collaboration with Levi’s.
To this day, the denim moment remains a touchstone of the early 2000s cultural zeitgeist. “I don’t know, man, you could kind of rock that today,” Timberlake told former ‘NSYNC bandmate Lance Bass on the latter’s podcast series “The Daily Popcast” in 2020.
Yes, the fashion moment still lives on in infamy. But the 2001 American Music Awards wasn’t the only couple style showcase for Timberlake and Spears.
Despite their contrasting approaches to fashion, Timberlake and Spears epitomized the early 2000s. Spears regularly embraced the formfitting, hyperfeminine, sparkling styles that elevated the princess of pop to a new echelon of superstardom.
Timberlake, for his part, favored relaxed fits, layering and even the frosted tips hairstyle that became synonymous with the era.
Beyond the glamour of the red carpets they shared, the duo’s relationship, which ended abruptly in 2002, was complicated. In her 2023 memoir, “The Woman in Me,” Spears revealed difficult moments between the pair, specifically referencing a 2001 pregnancy.
“I always expected us to have a family together one day,” Spears wrote in an excerpt from the book. “This would just be much earlier than I’d anticipated, but Justin definitely wasn’t happy about the pregnancy. He said we weren’t ready to have a baby in our lives, that we were way too young.”
Spears continued: “I don’t know if that was the right decision,” she continues. “If it had been left up to me alone, I never would have done it. And yet Justin was so sure that he didn’t want to be a father.”
Following their split, Timberlake released the track “Cry Me a River” and its accompanying music video, both of which fueled rumors that Spears had cheated on Timberlake, a subject examined in the 2021 documentary “Framing Britney Spears.”
Later, in 2021, Timberlake made a statement regarding the relationship: “I have seen the messages, tags, comments and concerns and I want to respond. I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn, or did not speak up for what was right,” he wrote in a social media post at the time.
The rise of Y2K fashion and revival of trends from the era by Gen Z has certainly sparked a renewed interest and fascination with the trend-setters and stars who defined the early 2000s. Timberlake and Spears certainly set themselves apart from their contemporaries, not only for their respective fearlessness with fashion, but also the playful ways in which the two stars reveled in the designs of the time.