As for how the unique looks came together, Steven Gerstein, who styled NSYNC at the time, explained the process in a recent interview with Jezebel.
“Justin and Britney were dating at the time. We were in New Orleans when Britney and Justin were like, ‘We’re doing matching denim.’ And I was like, ‘How are you doing that? Who is doing that?'” Gerstein recalled. “We wound up taking the Costume National suit that Justin wore for the Celebrity album cover. We remade it in denim. Conversations with Levi’s were happening at the same time and Britney was working with Kurt and Bart. We had some crossover contacts at Levi’s, so it went from being an idea to it being made within days. The rest is history.”
While they were two of the biggest pop stars in the world in that moment, Gerstein remembered the former couple as “just two kids, wanting to do something cool, and being super cute, matching. It was kind of like their prom. They had an idea, and we did what they wanted as opposed to the other way around.”
To revisit the iconic fashion moment, keep scrolling for a digital stroll down memory lane!
