Britney Spears reveals story behind iconic double-denim matching outfit with Justin Timberlake

Britney Spears has reflected on the iconic double-denim outfit she wore alongside her then-boyfriend Justin Timberlake in 2001.

Spears and Timberlake – who were dating at the time – attended the American Music Awards together and quickly made headlines with their showstopping outfits. The pair wore matching head-to-toe denim looks, including a blue denim cowboy hat on Timberlake.

The instantly recognisable double-denim moment has gone down in sartorial history, with many people replicating the look for Halloween couple costumes.

Reflecting on the starry fashion moment, Spears writes in her new memoir The Woman In Me that she initially suggested the idea to Timberlake and their stylist as a joke.

“I still can’t believe that Justin was going to wear denim and I said, ‘We should match! Let’s do denim-on-denim!’’” she explained.

“At first, honestly, I thought it was a joke. I didn’t think my stylist was actually going to do it, and I never thought Justin was going to do it with me. But they both went all in.”

Spears continued: “The stylist brought Justin’s all-denim outfit, including a denim hat to match his denim jacket and denim pants. When he put it on, I thought, Whoa! I guess we’re really doing this!”

At the time, the pop star was a newly famous pop sensation and Timberlake was an international heartthrob as the frontman of boy band NSYNC. Together, they would attend multiple red carpet events in the years they dated, from 1998 to 2002.

“Justin and I were always going to events together,” Spears said. “We had so much fun doing the Teen Choice Awards, and we often color-coordinated our outfits. But with the matching denim, we blew it up.”

Britney Spears and Justin Timberlake photographed at the Shrine Auditorium in LA in 2001


Spears explained that the denim corset she wore to the event was so tight that she thought she might fall over on the red carpet.

“I get that it was tacky, but it was also pretty great in its way, and I am always happy to see it parodied as a Halloween costume,” she said.

Spears went on to address the criticism that Timberlake faced for wearing the matching outfit.

“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.’  And that’s exactly right. We were giddy, and those outfits reflected that,” Spears wrote.

The pair began dating after meeting on the set of the All-New Mickey Mouse Club in 1992.

Elsewhere in the memoir, Spears wrote about her decision to get an abortion after she became pregnant while dating Timberlake.

Britney Spears and Justin Timberlake photographed in 2002

(Getty Images)

“It was a surprise, but for me, it wasn’t a tragedy. I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I’d anticipated” she said of the pregnancy.

“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 appeared to imply that she decided to get an abortion because it was what Timberlake had wanted her to do.

“I’m sure people will hate me for this, but I agreed not to have the baby. I don’t know if that was the right decision,” she wrote in the memoir. “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.”

“To this day, it’s one of the most agonising things I have ever experienced in my life,” she said.

The Independent has contacted representatives for Timberlake and Spears for comment.

The Woman in Me is out now. You can read The Independent’s four-star review of the memoir here.