The Y2K Fashion Faux Pas Britney Spears Wished She Didn't Make With Justin Timberlake

If you opened a history book based purely on legendary pop culture moments and flipped it to a chapter titled "2001," you would likely see Britney Spears and Justin Timberlake dressed head-to-toe in double denim at the American Music Awards. There's a good chance those somewhat ridiculous outfits will live on in infamy for the rest of recorded history. The backstory behind those looks isn't the most surprising confession in Spears' memoir "The Woman in Me," but it is interesting to hear her take.

In her memoir, Spears wrote, "I still can't believe that Justin was going to wear denim and I said, 'We should match! Let's do denim-on-denim!' At first, honestly, I thought it was a joke." Spears didn't expect Timberlake or her stylist to go along with the idea, but it all became real when Timberlake received his denim hat, pants, and jacket. Spears continued, "When he put it on, I thought, Whoa! I guess we're really doing this!"

The couple had matched the colors of their outfits before, although the double denim ensembles were next-level. Spears didn't completely disavow the looks, however. She said, "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."

Another pair of celebs rocked their own denim on denim looks

Something else Britney Spears said about her and Justin Timberlake's double denim outfits at the 2001 AMAs was how it was proof of their love. Although Timberlake was made fun of for the look, Spears said, "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."

Another celebrity couple (of sorts) wore their own matching, double-denim outfits to an awards show. Although their official relationship status was very murky at the time, Katy Perry and Riff Raff channeled Spears and Timberlake at the 2014 VMAs — adding a little extra bling onto their versions of the denim outfits. 

At the time, Perry replied to one of Spears tweets on X, formerly known as Twitter, and said, "@britneyspears I did my best impression, hope u likey!" The "Toxic" singer tagged Perry and replied, "Just when I thought the denim dress had retired ... you bring it back! You looked amazing tonight bb ;) ."

*NSYNC's stylist called the 2001 AMAs Spears and Timberlake's 'prom'

In 2015, Britney Spears shared her appreciation when stylist Monica Rose had her children dressed to the nines in their own Spears-and-Justin-Timberlake-esque double denim for Halloween (via Instagram). Although Spears' Instagram account is now private, Marie Claire reported at the time that Spears posted one of the photos of the kids on her own account and included the hashtag "#britneyandjustinforever" in the caption.

A stylist for Timberlake's band *NSYNC, Steven Gerstein, was interviewed by Jezebel about Timberlake's denim suit about 19 years after the "Pusher Love Girl" singer and Spears changed pop culture forever. "It's so funny," Gerstein told the outlet, "I sometimes forget that I did it, and forget that it is so iconic, because on my timeline it was one of a million outfits I had to come up with. That one just got a lot more traction than the rest." Gerstein confirmed that Spears and Timberlake chose the outfit idea, unlike how it usually goes, where the stylists pick what the celebrities wear. He even said, "It was kind of like their prom."

Costume designers Kurt and Bart designed Spears' denim dress, and it was auctioned by NateDSanders.com in 2016, selling for over $7,000. If you want to affordably, yet subtly commemorate those AMAs 'fits, you can find ways to style denim on denim without looking like Spears and Timberlake circa 2001.