One Woman's Hunt for Britney Spears and Justin Timberlake's Matching Denim Outfits

By Maria Sherman | June 11, 2020 | 1:55pm

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One Woman's Hunt for Britney Spears and Justin Timberlake's Matching Denim Outfits

Two years into their reign as it-couple king and queen of teen pop, Britney Spears and *NSYNC’s Justin Timberlake arrived at the 2001 American Music Awards in what would become two of the most iconic ensembles in red-carpet history, both of them in head-to-toe denim. Her Kurt and Bart patchwork bustier gown was accessorized with a sparking rhinestone choker and wrist cuff, her handbag melding the two elements. His look was a bit more distressed, a bit more rugged: a matching denim suit—a Canadian tuxedo that screamed American youth—topped with a cowboy hat, a reference to their shared Southern roots.

Britney and JT ruled the peculiar Y2K period, dominating the charts just before the music industry collapsed on itself. In some ways, these denim looks have become a symbol for that time period, when pop princesses and boy bands ruled. For others, it is simply the definitive look for an era of questionable fashion, where skirts over jeans balanced on hipbones was considered acceptable wear. Either way, their denim-on-denim is legendary. Two decades removed, it has become an easily-recreated Halloween costume. Celebrities, too, have parodied the look: by Victoria’s Secret supermodel Devon Windsor and her husband Jonathan Barbara of Alexis Apparel, and most notably, by Katy Perry and Riff Raff at the 2014 MTV Video Music Awards. The look’s legacy endures.

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And so I went looking for what happened to these iconic fits after their 2001 award show debut. Social media has allowed fans some (highly edited) insight into where Britney and Justin are today, but what happened to the clothing? That answer is a bit more complicated.

In doing research for my first book last year, LARGER THAN LIFE: A History of Boy Bands from NKOTB to BTS, I learned that Britney’s gown sold at auction in 2013. Spears memorabilia is highly collectable—no shocker there—so it should come as no surprise that Nate D. Sanders Auctions was able to sell the gown to an undisclosed buyer for $7,199. (Sanders did not return Jezebel’s request for comment.) It is possible that the Spears estate gave Sanders the dress in the first place to sell—most clothing worn on red carpets is either returned to the designer or gifted to the celebrity wearing it, after all—but that has not yet been confirmed. At the very least, someone purchased it in the last decade, and that’s enough closure for me.

Searching for Justin’s suit yielded no such results. Endless perusal of fan pages led nowhere. The closest I could get, it seemed, was an AngelFire page from 2001 featuring a transcribed interview with *NSYNC’s hairstylist. Tragically, it included nothing about his or the group’s fashion. When it became clear that I was not having any luck, I did what any sane person would: I combed through the liner notes of *NSYNC’s 2000 album, No Strings Attached, one of the best-selling records of all time, and searched each name until one appeared to be a stylist. After a few hours of detective work, I found an interview with costume designer Steven Gerstein in the New York Post from 2003 about pulling looks from discount retailers. And then it clicked: This was the guy. His career must have changed direction post-boy band explosion, but this was him.

And so I cold-emailed Gerstein, and he agreed to an interview. Turns out, he designed Timberlake’s denim suit. After the 2001 American Music Awards, it ended up sitting in his garage for years, like many priceless pieces of *NSYNC iconography. Where they ended up is still a mystery, but it did lead to a surprising conversation with a man responsible for *NSYNC’s fashion—and, through their influence, many of the late 1990s and early 2000s wildest trends. That conversation follows, and has been edited and condensed for clarity.

Hey Steven! I’m on the hunt for Justin Timberlake’s denim suit from the 2001 American Music Awards, and you styled *NSYNC for much of their short career. Before we get into that specific fit, I’m curious: How did you get started in fashion?

I lived in New York. I went to FIT for design. I thought I was going to be the next [Jean Paul] Gaultier. [I] wound up getting a job at MR Magazine, an industry men’s wear, fashion garment district magazine. I had a friend who worked at Uptown Records—she was like, “We have this artist whose really tall, you’re really tall, maybe something will work out, can you pick out some clothes for him?” I didn’t even know what a stylist was at the time. The concept hadn’t really clicked to me yet. But the money was insanely good back then, when the music business was booming. The artist was Montell Jordan. The video was “This Is How We Do It.” So I came to L.A. and saw this entire new world.

This is the late ’90s?

This is 1997, 1998. I moved to LA in 1999. That’s about the time an editor of Teen People had been styling *NSYNC. As they started to become more popular here in the states [after first blowing up in Germany], there was a conflict of interest. She couldn’t work for the magazine and style one of the big bands that was eventually going to be on their covers. So I got called in basically to unpack a box, steam the clothes, and get these boys dressed. I wasn’t even registering the concept of “boy band” at the time. It wasn’t really a term, as much. It was really just them and Backstreet Boys.

So I styled these guys and I remember my assistant and I showed up in our crazy stylist clothing; we used to dress nuts. They were in their late teens, I was probably in my 30s at this point, and they were like, “Boots? Wow! Ripped Jeans? Wow!” I remember thinking: “Where are these kids from that they don’t see stuff like this?” And then I realized that I work in music fashion, these are young boys. We had a great shoot. I think they were accustomed to being catered to and I was just like, “No way, you can’t wear that.” And at that photo shoot, Ibrahim [Duarte], their road manager at the time, was like, “Hey, the guys think you’re really cool and want to know if you’d want to do a couple more things with them.” And I’m still like, “Whatever, boy band, I don’t get it, but yeah, sure, work is work.” He handed me a global tour book and said, “Any of these cities look interesting? You wanna come give them some clothing?” And it was like Paris, Tokyo, Moscow, everywhere on the planet. I was on board from that moment on. And we became a touring circus. Twenty of us went everywhere.

What was the first look you styled for *NSYNC?

It was an award show they were doing. They wore all beige Kenneth Cole suits. They all had the same suit, which I didn’t understand at the time. Immediately I was like, “Why don’t you mix it up?” And I could see management getting like, “They always wear kind of some of the same thing.” I think they liked that I never buckled to that concept, and they saw the possibility of having individual personalities. From then on, the styling experience was that I would bring in rooms full of clothes and I knew after a while what each guy would gravitate towards. And then it became a concept of, “Hey, I have this idea, I want to dress like this,” or “I saw this great leather jacket, can you get me that and then you can do the rest of the outfit?” It ended up being a really interesting partnership.

It was kind of like their prom… so I called people in New York and said, ‘Go buy 50 pairs of vintage Levi’s.’

Are there any especially memorable *NSYNC looks you styled, maybe from a music video or red carpet or infamous paparazzi shot?

Obviously the denim look comes up all the time. It was such a no-brainer. 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?” 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. It’s so funny, 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. Obviously, the Britney/Justin connection added fuel to the fire, but it was a really organic… it was 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. In this case, they were like, “We want to do this,” and Kurt and Bart and I collaborated. I remember I had people in New York so I called them from New Orleans and said, “Go buy 50 pairs of vintage Levi’s.”

The woman who sewed it together was a woman named Linda Stokes. She was making clothing for everyone. She was the only seamstress in LA that had a 24-hour operation going on. She was fantastic, the most humble and accommodating woman. She was about 45 minutes outside of the city, which is always a drag, but you could call her at literally five in the morning and say, “Oh, god, I need a wedding dress by 9 a.m.,” and you would have that wedding dress. You’d have to drive out to Woodland Hills to get it, and she never delivered. I think the one time we asked to have it delivered she was like, “Oh, you don’t know? That’s not part of my service.” And that drive to Woodland Hills became a normal thing. I think if you were to ask any stylist in LA, from the late ’90s to the mid ’00s if they know Linda Stokes, everyone has taken that drive on the 101 at three in the morning. We would get there and there would be cars outside from every stylist we knew. When it was award show season, she was just packed. If it wasn’t for Linda Stokes, a lot of LA wouldn’t have gotten dressed at the time.

So you sent her the design, and she put the suit together?

She sewed, after I sent her the suit. *NSYNC were still heavily Orlando-based at the time, so after every tour or iconic performance we would bag everything up, photograph it, and send it to [their manager] Johnny Wright’s office. I don’t know where it went. I remember at one point when they broke up, I still had a garage full of clothing. I had that suit for the longest time in my garage. Sending it back was like, “Oh, OK. I’ll never see you again. Bye, denim suit!” I remember being like, I wish we did the pants… still, trying to finesse a suit I know no one would ever wear again. “Oh, I wish I did the sleeves a little bit shorter, oh, I wish the flare was a little bit…” And I remember the guys who worked on my team were like, “Just get it in the bag and get it out of here.” It was bittersweet, a symbol that an era was ending. Not only for them, but it was like, “Oh, OK, I guess I just ran around the world with these teenagers?” Then I just went into regular styling.

Do you have any idea where the suit is now?

I sent it back to management. They were really starting to archive things. At one point it was like, “Put everything in a box and send it to Orlando.” Look, I dressed them crazy. I fully acknowledge that. At the time, it didn’t seem that crazy. But looking back, it’s like, “Whoa, what were we doing?” We were just nuts, wearing whatever. And we had access to whatever we wanted. Sure, their 14-year-old fans didn’t know that they were wearing head-to-toe Dior from the runway, but we did, and we thought it was cool. They liked meeting designers and they liked being part of this bigger global thing. So we started to archive it. It was when polaroids were still a thing and we had polaroids of everything. Every shoe. We had so much going on that we had to have a catalog. I wonder where that catalog is now… I’m sure it’s somewhere in Orlando, but I’m not sure.

When things wound down, [managers] Melinda [Bell] and Johnny Wright were very diligent—they wanted to make sure that things weren’t just out in the ether. They really needed to control the message, control the flow of information about *NSYNC. It made total sense. About a year after we shipped the final outfit, I found some [denim] jackets that we didn’t end up using that we made—I went on to work for Levi’s for many years after that—in their lobby in San Francisco. I can’t remember what tour they were from, though. I remember it was when we were like, “Wouldn’t it be great if you covered an entire denim jacket in rhinestones?” That was the beginning of the rhinestones thing, which then took over my life for many years. It’s like, what were we thinking at the time? “Let’s have guys cover themselves in metallic leather and rhinestone chaps!” Everyone I knew, at one point, put a rhinestone on an *NSYNC outfit.