Skip to content

Justin Timberlake Has a Confession About That Iconic Denim Look

The *NSYNC singer and Britney Spears wore the notorious matching outfits back in 2001.

Even though Britney Spears and Justin Timberlake only dated for a couple of years in their early 20s, the celebrity couple has gone down in pop culture history. That's thanks, in part, to one night in particular when they wore matching outfits to the 2001 American Music Awards. Spears and Timberlake's coordinating denim ensembles are one red carpet look that no one will ever forget—including Timberlake, because no one will let him.

The Hollywood Reporter recently held a virtual Songwriters Roundtable, featuring Timberlake, John Legend, Janelle Monáe, Mary J. Blige, and Leslie Odom Jr. When the musicians were asked about the early days of their careers, Timberlake brought up some of the outfits he wishes he could "skip over," and Legend jumped at the opportunity to bring up the notorious denim look.

Read on to find out what Timberlake confessed about the iconic jean outfits, and for more blasts from the past, here are 15 Onscreen Couples You Totally Forgot Dated in Real Life.

At the 2001 AMAs, Timberlake wore a true denim tuxedo and Spears donned a jean gown.

Britney Spears, Justin Timberlake denim outfits
Frank Trapper/Corbis via Getty Images

Timberlake and Spears wore their denim looks to the AMAs in January 2001, making the outfits 20 years old this year. For their head to toe jean looks, Spears wore a denim gown and a denim purse, accessorized with plenty of sparkly jewels, while Timberlake went with a denim suit with a denim cowboy hat and some very early aughts sunglasses. Spears' dress was made by costume designers Kurt and Bart, who worked with her regularly at the time, and Timberlake's outfit was made by designer Steven Gerstein, who had been working with *NSYNC.

In an interview with Jezebel in 2020, Gerstein said that the outfits were Timberlake and Spears' idea. "It was just two kids, wanting to do something cool, and being super cute, matching. It was kind of like their prom," he said. "They had an idea, and we did what they wanted as opposed to the other way around."

And for more iconic celebrity style moments, check out Celeb Red Carpet Photos From 2000 You Have to See to Believe.

Timberlake knows he'll never live it down.

Justin Timberlake at the premiere of 'Cafe Society' in 2016

During the Hollywood Reporter roundtable, Timberlake, who's now 40, was asked if he looks back on the music he was writing early in his career and how far he's come.

Timberlake said a lot of his early work is overshadowed by what he wore instead. He said, "I confess that there was maybe a period in the '90s where I could skip over some of the outfits that were public, but the internet will never…" Then, Legend interrupted with, "Denim on denim on denim on denim that will never be forgotten!" Timberlake replied, "Thanks, John. Uh, no, the internet won't allow me to forget them. So it's all good."

For more celebrity news delivered right to your inbox, sign up for our daily newsletter.

This isn't the first time Timberlake has spoken about the denim looks.

Justin Timberlake, Joey Fatone, Lance Bass in 2000
Everett Collection /

While appearing on fellow *NSYNC member Lance Bass' podcast, The Daily Popcast, in March 2020, Timberlake spoke about the denim outfits and stood by the style decision. "You can kind of rock that one today," Timberlake joked (via E! News). He added, "You do a lot of things when you're young and in love."

While it doesn't seem that Spears has commented on the outfits herself after all these years, she did repost an Instagram of stylist Monica Rose's kids dressed up like Spears and Timberlake for Halloween in 2015.

And if you remember this music era fondly, check out 19 Photos From the 1999 VMAs That'll Blow Your Mind.

The outfits were famously recreated years later by another famous duo.

Riff Raff, Katy Perry 2014
Jaguar PS /

In 2014, Katy Perry and rapper Riff Raff attended the MTV Video Music Awards together wearing new versions of Spears and Timberlake's ensembles, with Perry's dress designed by Versace. The singer tweeted at the time, "I must admit my outfit is a result of my love for nostalgia and my Tumblr addiction." And for more nostalgia, check out Priyanka Chopra's Adorable Throwback of Herself at 17.

Lia Beck
Lia Beck is a writer living in Richmond, Virginia. In addition to Best Life, she has written for Refinery29, Bustle, Hello Giggles, InStyle, and more. Read more
Filed Under