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One cannot look back on 2001 R&B/hip-hop without paying homage to the fits, the fits, the fits! Designer monogrammed wigs, bedazzled denim from head to toe, the occasional inexplicable trend (Nelly, looking at you), and, of course, Destiny’s Child never leaving the house without three glamorous variations of the same fabric.

“[Hip-hop fashion] was creative and custom,” says Derek Lee, former stylist to R&B icon, Aaliyah. “It wasn’t driven totally by designers, you could still show up with some street stuff and it’d be acceptable.” Lee, who styled the beloved singer from 1996 to 2001, pioneered the “sensual tomboy” aesthetic, central to today’s fashion landscape, and evident in the wardrobes of R&B stars like Ciara, Teyana Taylor and Rihanna.

Lee recalled his own customizing experiences, adding glitz to streetwear pieces for the late singer. “We were flying to Paris and I’d be bedazzling Enyce sweatsuits for Aaliyah,” he explains. Lee paid homage to fellow stylist June Ambrose for her work with Missy Elliott in further establishing the craze surrounding bedazzled pieces.

Ambrose, who styled over 200 music videos, was Missy’s right-hand woman, costume designing for every major Missy Elliot production including “Get Ur Freak On,” “The Rain (Supa Dupa Fly),” “One Minute Man,” and “Lose Control.” She was a go-to designer for R&B/hip-hop heavyweights including Diddy, Jay-Z, Mary J. Blige and Mariah Carey, and currently works as a creative director for Puma.

“We didn’t have a point of reference that came before us,” explains Ambrose. “We took the risk for the future.” The “Rain” designer discussed the role of late ’90s to early ’00s designers as trailblazers, bursting through barriers between high-end labels and R&B/hip-hop culture. “I bridged high fashion with urban music,” says Ambrose, “What felt so rebellious was taking a high fashion piece, and still keeping the same demeanor and swag that you wore in your neighborhood.”

Dionne Alexander, the hairstylist behind Lil Kim’s monogrammed wigs and Mary J. Blige’s ’90s updo’s, agrees. “Look how free we are here,” Alexander says. “It was very exciting, we were able to be extremely creative and we had to pull it from within. We didn’t have Instagram, we had to go out and get magazines.

“Tre Major, hairstylist to legendary celebrities including Aaliyah, Mary J. Blige, Patti LaBelle and Naomi Campbell, says the early ‘oos was “the best” era for fashion and hip-hop. “I was like an architect on the outside,” Major explained. “Building the visuals, landscaping and making it gorgeous.” Major was responsible for ushering in the lace-front wig into the world of R&B/hip-hop. “[The other stylists] were just geek because they never seen anything like it,” says Major. “Now you can find a lace front wig on every corner, every boutique, every website.”

On the 20th anniversary of these iconic, enduring year in fashion, Billboard caught up with the architects of the era, June Ambrose, Derek Lee, Tre Major and Dionne Alexander, to discuss some of the most memorable looks in ’01 R&B/hip-hop and how these moments shaped the culture for decades to come.

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Missy Elliott’s “Get Ur Freak On” bedazzled denim

In ’01, rhinestones were all the craze, and we have June Ambrose to thank. “It was all about making Missy a rock star,” says Ambrose. “I got her hooked on rhinestones — and once that happened, forget about it.” The 200-time music video stylist says the glittering look from Missy’s Dave Meyers directed video was meant to create a dichotomy between Elvis-like glamour and sportswear. “The jean jacket silhouette was very comfortable and relatable to her, but taking a Bootsy Collins over the top approach is what made it really tangible and special.”

 

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Aaliyah’s “More Than A Woman” Chanel catsuit

Aaliyah’s Dapper Dan-designed faux Chanel catsuit from the “More Than a Woman” video is one of the late singer’s most iconic moments. “I knew that it was going to be a feature, that it would be striking, if it was different from anything she has done before,” says Lee. The decision to choose Chanel was a step away from edgier brands like Dolce & Gabbana and Roberto Cavalli, which the sweet singer was typically dressed in. But why not have Chanel design the piece themselves? “[The major brands] didn’t want to be associated with rap music and this street culture,” explains Lee, “That’s why we had to create our own stuff or have it knocked off by [Dapper] Dan.” When Aaliyah saw the design, Lee says she was feeling it. “I had decided to move Aaliyah into almost a cartoon character,” he tells Billboard. “I was going down to Little Tokyo and getting all these anime books and had this entire idea.”

 

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Lil Kim’s monogrammed wigs

Monogrammed tresses have popped up on the heads of the rap’s most iconic first ladies, including Nicki Minaj and Cardi B — but similar to countless other signature hip-hop trends, it started with Lil Kim as the blueprint, and hairstylist Dionne Alexander the architect. “The inspiration totally comes from [Lil Kim] and who she is,” says Alexander, the mastermind behind Lil Kim’s Versace wig and equally iconic blue Chanel wig. “It was such a flow of creative energy, like a power that was coming through.”

Alexander recalls coloring the Chanel wig Lil Kim wore for Manhattan File Magazine late into the night, until 5:00 in the morning. “I went to the art store and got trace paper and created the logo, then I cut it out.” And her secret? Black magic marker. “With the Versace wig,” Alexander says, “She called me and left this message on my machine that I literally kept for years. She went nuts, and it was the same with the Chanel.”

Alexander says the present-day response to both wigs is surprising. “It’s more of a buzz now than it was then. I’m so shocked at how many people call me about it now.”

 

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Outkast’s ‘So Fresh’ and ‘So Clean’ looks

The evolution of men’s fashion in hip-hop is inextricably linked to the genius duo best known as Outkast. The pair defied longstanding tropes of how rappers were expected to present themselves and sent the media into frequent frenzies, with their delightfully shocking red carpet looks. In the “So Fresh, So Clean” music video, the eccentric Georgian duo rock a myriad of hairstyles, from a sleek, flipped perm, to a combed out, asymmetrical afro.

“That’s some Southern, playalistic s–t right there,” says Lee, in reference to the pair’s ’01 look. Alexander says Andre 3000 and Big Boi “revolutionized male confidence” through their unapologetic expression of creativity. Of Andre 3000, Major says, “He took a real gamble and went for it, just being his true artistic self and everyone loved it.”

 

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Macy Gray’s Vocal Dress at the MTV Video Music Awards

It was the dress seen (and read) around the world. Macy Gray, a performer known for her unconventional style and music, decided to transform her award show dress into a walking billboard. “That was totally Macy’s idea, I just had to execute it,” says Ambrose, the designer of Macy’s immortal dress. “Working with Macy Gray was so much fun because she was an anomaly,” Ambrose remembers. “In that moment, it was important that she sold albums, and she had she wanted to capitalize on the moment. It’s like, where’s the return on the investment? I’m getting hair and makeup and spending money on wardrobe. Is it gonna help me sell records? We wanted to just make sure that it did.”

 

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Destiny’s Child’s coordinated camo

There are few things more memorable about the late ’90s and early ’00s than DC3’s coordinated looks. Whether it was award shows, music videos or MTV appearances, you caught caught the trio out and about without perfect coordination. “Tina Knowles strikes again,” says Ambrose, of Beyonce’s mother and the group’s resident designer. “Utilitarian was such a celebration of being tough and dominant,” Ambrose explained. “It showed females in military can be sexy, that it’s not just a man’s game.” Major drew comparisons to another always coordinated, ever-influential girl group. “Every time I looked at them, I saw the modern day Supremes,” he said. “Everyone wanted to follow the camouflage trend.”

 

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Nelly’s inexplicable face band-aid and double headbands

While there are countless rumors circulating the World Wide Web about the explanation behind Nelly’s little white Band-Aid and criss-crossed headbands, none have yet to be verified. But regardless of the backstory, Nelly’s creative face accessory was all people could talk about. “He created his own thing, like a left-eye kind of moment,” says Major, who remembered considering rocking a Band-Aid himself. Ambrose says the bandage symbolized a “thug badge of honor,” as iconic to Nelly as eye black is to football players.

 

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Alicia Keys’ beads and cornrows

Before Alicia Keys arrived on the scene, cornrows and beads were seldom seen in mainstream music. Ambrose, who styled Alicia in the early years of her career says the piano extraordinaire’s team always kept her identity in mind. “We wanted to always keep a sense of that New York girl and celebrate all the things that that spoke to her blackness,” says Ambrose. Not only was Alicia’s hair aesthetically striking, it also played a roll in representation of black women’s natural tresses. “Universally, it told other young black girls and it’s okay to wear your braids and your beads,” explained Ambrose. “That this isn’t a Bo Derek moment, this is an African moment.”

 

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Mary J. Blige’s avant-garde “Family Affair” wigs

It’s hard to say what part of the “Family Affair” experience was most unforgettable. Was it the futuristic outfits? Iconic choreographed moves? The fact that Mary basically invented three new words? In the world of fashion, it was most definitely the wigs. Tre Major, Mary’s long-time hairstylist, says the chart-topping singer was ever-evolving, setting trend after trend along the way.

“I gave her edge and femininity,” says Major. “I named that wig the Marvin Martian,” Major says of Mary’s salt and pepper avant-garde wig, a nod to the Looney Tunes character. Major says he custom made the wig on the R&B diva, since her head was “so small” compared to the mannequins. “She was the best muse because she was so daring,” he explains. “She trusted me.”

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