Oh, the early aughts! Justin Timberlake revealed in a new interview that he regrets the matching double denim outfit he wore with then-girlfriend Britney Spears 15 years ago at the 2001 American Music Awards.
During an appearance on the Australian talk show The Project, the “Can’t Stop the Feeling!” singer, 35, was asked, “What have you learned about the industry that you didn’t know when you were in ‘NSync that you know now?”

Timberlake replied, “If you wear denim-on-denim, it will get documented. You know what, I don’t think I could even bring that back.” He then added, “I’m going to go out on a limb and say if it’s worn properly, denim-on-denim could be [brought back].”
The entertainer was then asked which celebrity he thinks would be able to revive the dated look, to which he quipped, “Not Donald Trump.”
As fans know, Timberlake and Spears, 34, arrived at the 2001 AMAs in matching head-to-toe denim outfits that have since been lauded as iconic. Approximately two years into their relationship, the pop stars, who were both 19 at the time, walked the red carpet in the eye-catching jean ensembles. Spears rocked a strapless patchwork denim dress, which she paired with a denim purse and a rhinestone choker, while her boyfriend donned a denim blazer, jeans and a light-wash fedora.
“Did you see the outfits we wore?” the “Cry Me a River” crooner quipped on The Project, referring to his former boyband, ‘NSync. “It was such a crazy time and the world was different, the music industry was different. It was just a different time.”
Timberlake and Spears separated in March 2002 amid rumors that she cheated on him. The Trolls actor is now wed to actress Jessica Biel, with whom he shares 19-month-old son Silas. Spears shares two sons, Sean Preston, 11, and Jayden James, 10, with ex-husband Kevin Federline.
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