June Ambrose on Customizing Timberlands for Busta Rhymes and Finding Retro Pumas For Missy Elliott

Consider June Ambrose the fashion fairy godmother of hip-hop.

There is plenty that the costume designer and multi-hyphenate has contributed to in both industries. As Jay-Z’s stylist, she is responsible for keeping the music artist looking executive-level cool both onstage and off camera. And since 2021, Ambrose has held the position of creative director of women’s basketball for Puma. Over the years, she has done costume design for everyone from Mariah Carey to Will Smith in addition to authoring her own style tome, the 2006 “Effortless Style” and hosting the VH1 reality show “Styled by June” in 2012.

But it’s the music videos of hip-hop’s halcyon days of the late ’90s and early 2000s that have cemented Ambrose’s status as a bona fide music legend. Working side by side with director Hype Williams, the costume designer was responsible for creating the memorable — yes, iconic — looks of the Y2K/TRL era, from Missy Elliott’s infamous garbage bag to paying full homage to Eddie Murphy’s “Coming to America” in the Busta Rhymes film for “Put Your Hands Where My Eyes Could See.” The videos became an integral part of bringing hip-hop to the fashion world, and vice versa.

“At the time, Black music and video were only being played on BET and our goal was to get MTV and VH1 to play the music,” Ambrose told FN in an exclusive interview. “The only way we could do that was to create imagery that was provocative and commercial and it felt like us.”

On the eve of hip-hop’s 50th anniversary, Ambrose went even further into her costume design archives to give FN the scoop on the best shoe moments from those unforgettable music videos.

Busta Rhymes

“When I was working on the music video “Put Your Hands Where My Eyes Could See,” I custom designed every piece he wore, including the footwear. I did this custom lamé robe, and I had this idea to do a customized matching shoe, like any proper woman would do. I was really playing with gender fluidity and I loved the idea that we were re-designing something that was so eccentric with something that was so tough. When you thought about what was the toughest shoe you could wear at that time on the streets, it was the Timberland [boot]. I brought the shoe to a cobbler and said, ‘I need you to take these boots apart and cover them in this lamé fabric.’ As we came back with more pairs, the price went up because he realized that this was something that was going to catch on. We really opened a can of worms. After that video, Busta would not go on stage without the matching Timberlands to every customized look. It was disruptive and sexy and provocative and very hip hop.”

Missy Elliott

“Everything Missy wore had to be tied back to a sneaker. When I first started working with her, it was all about finding the most nostalgic footwear pieces. I remember using the Puma California sneaker in the music video for ‘The Rain (Supa Dupa Fly).’ Missy is a collector of sneakers, so at the time, to find something that was super retro but edgy and new and fresh — because we were bringing it back — became a classic again. It was that one scene where she is on the hill, in this customized leather
jogging suit that I designed for her. It was mint green with the matching California sneakers to go with it. And I remember after that video people started saying ‘Ooh! That retro California Puma! I’m going to bring those back.’ That’s how things worked in hip-hop culture. We would literally feed off each other. It became sport, to find what was not being used and reimagine it.”

Puff Daddy and Mase

“‘Mo’ Money Mo’ Problems’ was one of my favorite videos to design. At the time, Black music and video was only being played on BET, and our goal was to get MTV and VH1 to play the music. The only way we could do that was to create imagery that was provocative and commercial and felt like us. I think [Diddy] recognized how important it was for us to not be so predictable, that it was going to take some fearlessness. But I had to meet them halfway. The sock was a Nike Air. I called it the sock — certain footwear pieces were Bible. This is the foundation. It said Harlem, it said street, it was the space boot of the future. Every artist from every borough related to this sneaker.”

Nas

“There was a lot going on in that video. We were recreating the iconic movie ‘Casino.’ Character development was really my approach to everything. I was able to convince a lot of hip hop artists — my muses, I would call them — I would say, ‘There’s nothing you can’t thug out.’ If you’re wearing a pink suit, you can definitely pull off a white shoe with no socks. At the time, that was not the street thing to do, but when I gave them context, I think it changed the narrative. Street culture started to look at hip-hop not as just one singular conversation, it became a broader conversation, you started to see it more in the fashion space.”

DMX

“They opened up the scene in these python leather suits, it was kind of this Shaft moment. I remember pairing it with Timberlands to really ground it and make it feel relatable. 

When I first met DMX, Hype Williams brought him into the costume design department, we were working on “Belly.” He was wearing a padlock and he was growling at me. He was like no one else and I learned such a valuable lesson in meeting him in that moment. Never judge a book by its cover. Here I am thinking there is no way I’m going to ever be able to work with someone who is growling at me. This man was the most professional the most talented, the most on time, the most kind, warm hearted actor – not just rapper – that I’ve had the pleasure of working with. He proved us all wrong.”

For a look at the 50 most influential hip-hop artists in footwear, click here.