A timeless look? Justin Timberlake doesn’t regret wearing matching denim outfits with his then-girlfriend Britney Spears at the 2001 American Music Awards — and he thinks the outfits are still stylish in 2020.
Timberlake and Spears, 38, arrived at the 2001 awards show in coordinated head-to-toe denim outfits, which would become one of the most talked-about fashion moments of the early 2000s.
Bass, 40, recalled that the late ’90s and early 2000s — the time period that ‘NSync was at its peak — was a bad time for fashion.
“We’ve had our fair share of hairstyles and outfits back in the day,” the Out of Sync author said.“The late ‘90s were not great for style at all.”
Timberlake added that he found it hard to look back on his previous fashion choices. “If we could have only been a decade earlier when everything wasn’t so documented,” he said.
When Bass asked Timberlake what his favorite outfit and hairstyle from that time period was, the “Cry Me a River” crooner brought up his love of bandannas.
“Honestly, man, true confession,” Timberlake said. “I think I just started wearing bandannas because I couldn’t figure out what the hell to do with my hair.”
Although the Grammy winner is now defending his all-denim look, Timberlake wasn’t always on board with his past style choice.
Timberlake appeared on the Australian talk show The Project in November 2016, where he was asked, “What have you learned about the industry that you didn’t know when you were in ‘NSync that you know now?”
The “Mirrors” singer replied, “If you wear denim-on-denim, it will get documented. You know what, I don’t think I could even bring that back. I’m going to go out on a limb and say if it’s worn properly, denim-on-denim could be [brought back].”
Timberlake and Spears dated from 1998 until their split in 2002. The “Suit & Tie” singer went on to marry Jessica Biel, with whom he shares 4-year-old son Silas. Spears, meanwhile, shares her sons, Sean Preston, 14, and Jayden James, 13, with her ex-husband Kevin Federline. She is currently dating model Sam Asghari.
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