The glitz and glamour of entertainment is nothing without the people who dress today’s biggest stars. For “Who’s Behind the Clothes,” HuffPost spotlights stylists and costume designers who have delivered some of our favorite celebrities or characters’ most memorable looks.
Assistant stylist to some of today’s most prominent rappers, such as Future, Gunna, Roddy Ricch and more, Jenna Tyson is a powerhouse. Upon graduating from the Misa Hylton Fashion Academy, her plan was to take the editorial route and be at the helm of magazine covers. However, fashion legend Hylton saw a vision for Tyson that she didn’t know was possible. Tyson said, “Hindsight being 20/20, at the time, I was just like, ‘Why hip-hop? Why rappers? Why do I need to do these things when you know where my passion lies?’ But in the past five years, I’ve been so appreciative and had those conversations with her like, thank God, she saw what I didn’t see.”
Under Hylton’s tutelage, Tyson has worked with rapper-superproducer Missy Elliott and emcee Rapsody. Now, Tyson, 30, has landed her first independent client, Southern rap princess Flo Milli. In 2020, her singles “BeefFloMix” and “In The Party” took off on TikTok and through Twitter fancams. Tyson’s styling of Flo Milli has garnered mass praise from fans online, noting her standout looks at New York Fashion Week and unmatched creativity.
From Diesel and Hanifa to Tia Adeola, thanks to Tyson, Flo Milli stuns no matter what she’s wearing. Tyson’s greatest fashion hits with Flo include a custom, gold-encrusted leotard and feather train, featured in Flo Milli’s “Roaring 20s” music video. Lest we forget Flo’s jaw-dropping Paper magazine cover that combined hip-hop staples with patchwork denim, led by Hylton and assisted by Tyson.
Before Tyson became a stylist to the rap stars, she was a bright-eyed graduate of the Fashion Institute of Technology’s millinery program. Hailing from California, she moved to New York City during Rihanna’s “Rated R” era. In an effort to find the “So Hard” singer’s stylist, Tyson began researching fervently, landing upon Mariel Haenn. Tyson learned that Haenn acquired Rihanna as a client through none other than Misa Hylton, an award-winning fashion industry pioneer who has styled Lil’ Kim, Mary J. Blige and countless other Black icons.
“When I started researching Misa, I was just mind-blown from all the things that she had done, like her creative direction on the ‘Crush on You’ video,” Tyson said, referencing Lil’ Kim’s iconic 1997 music video. “I was like, ‘Mariel is great, but Misa Hylton’s who I want.’” In summer 2012, Tyson enrolled in Hylton’s critically acclaimed eponymous fashion academy — and there, Tyson’s life changed.
With the release of Flo Milli’s sophomore album “You Still Here, Ho?” and the hilarious skits that accompanied its rollout, the 22-year-old musician from Alabama became a style starlet. Ahead of Flo Milli’s debut tour launching Oct. 17, Tyson talked to HuffPost about her stylist journey, barriers that Black stylists have to overcome and what it’s like working with Flo Milli.
You’ve styled or assisted so many of Flo’s iconic looks, from her Paper magazine cover to her “Flosephine Baker” shoot. It’s no secret that Flo Milli is a creative visionary and conceptual queen, especially with her latest album rollout. How do you bring her visions to life with clothes and converge them in a way that makes sense for the artist, while continuing to push the needle?
[By] taking my time. I’ve worked with Misa for so long, so when it was time for that Paper magazine cover, it came together in so many different ways — but conceptually, paying attention for years to her creative process. When it was something that Misa allowed us all to come together and figure out the concepts for, it was me, her daughter Madison, and Misa that came together with those concepts. She has a very particular creative process.
We were working with Diesel, and they were sponsoring that Paper magazine shoot. Another good friend of mine, Nikki Martinez, is a consultant at Diesel and we came up with the upcycled piece of it. We needed so much denim, and they only had a roll, so Nikki was like, “We have all this old-season denim you can take.” That was just using your relationships, working with people, and not having an ego … It’s so stressful. It’s so crazy, then it comes together and you’re like, “Whew, OK, this was great,” especially being able to do all the aspects that we did, coming back to being a Black woman.
Flo has an amazing manager, who’s also a creative: Ebonie Ward. She is very integral in coming up with a lot of the creatives for Flo. She also is kind of like a silent killer, she watches, she plots, she puts things together. She was a huge part of Flo’s rollout. It’s a lot of work, but it’s passion-fueled because I’m fortunate enough to work with young, Black female creatives. It’s rare, and we’re continuing to push the envelope, we’re continuing to create opportunities in hopes that there are people that come behind us that want to do similar things. It’s an incredible opportunity to be able to work with someone like Ebonie, because we’re not just hypersexualizing everything that Flo is doing. Everything is so methodical, everything makes sense, and everything has passion behind it. That, in and of itself, is inspiring, because no matter the roadblocks or the hardships, you know that it has heart, it has soul. Sometimes Twitter responding gives you everything that you need. It’s better than getting writeups in fashion magazines. It’s like, “Well, we’re touching the people.” That’s the pulse, that’s the beat of the world.
How would you describe Flo’s style? You brought up an excellent point about how you’re leaning into the rap princess aesthetic, while also not trying to hypersexualize her. How do you make sure that you’re hitting the mark with each client, from Future to Gunna?
With Future and Gunna, I really just follow Bobby [Williams’] lead. He’s an incredible, one-of-a-kind stylist. It’s always nice to have that female and male perspective, so on Bobby’s projects, if needed, I just bring my female perspective for those things, and learn as much as I can from him because he’s worked with so many different people.
With Flo, she has great style; she has an evolving style. I think the best thing about her is that she loves so many different things, like a true creative does. We’re able to really have range and do a lot of different things as you can see from “Roaring 20s” to “Conceited.” She’s willing to tap into different aesthetics; the same way she has different sounds, she’ll play with different fashion, which I think is great. Her being so young, she has so much time to tap into every type of style that there is. We like to take our time with her, aesthetically, so that she has somewhere to go. If she just jumps into one aesthetic or something super sexy now, then where is she going to grow to? I think it’s important to let her be her age, work with that, and let it be organic. She’s a 22-year-old girl, so it’s letting her be 22.
Tell me about your journey to styling. What was your inspiration or impetus for entering the industry?
I’ve been in the business for 10 years. This is actually my 10-year anniversary of attending the Misa Hylton Fashion Academy, so that’s one of my first and most beloved mentors. I was one of the first students to ever attend her school in New York. I grew up in Orange County, California, I went to a performing arts high school, and I moved to New York when I was 21 to start chasing my dreams of being in fashion. My biggest inspiration at that time was “Sex and the City” and Patricia Field. It doesn’t get any better than that, just the range that she had on that show. I read an article at the time that said that her biggest inspiration was New York City as a backdrop, so I stopped everything in California and came to the big city.
Did you find that there was a gap in how West Coast style translates on the East Coast?
Being from Orange County or just Southern California, it’s very lax, chill, kind of like surfer vibes. I was more into vintage at that time, so I liked high fashion designers like Givenchy and Balenciaga, but also the classic silhouettes and girly, feminine aesthetics and proper dressing. It’s night and day. I think that the real style, the authenticity that they have on the East Coast, specifically in New York, was something that was most inspiring to me, especially because it’s so culturally diverse. I had never experienced that in this way, meeting Afro Latinos and Afro Caribbeans and seeing that kind of melting pot. What I love the most about New York is that it’s about the authenticity of your character and your style. So if you’re cool, you’re cool. If you can dress, you can dress. It wasn’t about like, all the extra fluff.
How would you characterize or describe your personal style now, and how has it shifted over the years?
It’s shifted pretty drastically. I tried to incorporate some of the older vintage that I have, but I’m a streetwear fanatic now: Japanese designs, some American fashion — everyone loves Rick [Owens]. But I love streetwear. I love oversized. I love Margiela, Simone Rocha. I like wearable art if it’s comfortable. Then, I like Black designers like Denim Tears, Marni for cozy vibes. I like streetwear because I think that we live in a time that’s hypersexualized, so I like to play on comfort and cool aesthetics, but I’m also a little bit older now. I’ve had my time wanting to be sexy and wearing dresses, but now I just like to be a little more serious and focused. I will switch it up and dress up if that’s what it calls for.
Who instilled your love for clothing and fashion?
My grandfather had always influenced me. He has really immaculate style. He’s very particular about his aesthetic, his clothes. He’s very clean; he loves everything about grooming, skin care and fragrance. I took a lot of that from him and that was like a big part of my childhood. When it was my birthday, he would always take me shopping. That instilled a lot of my pride about my style, and taking care of my material possessions.
Could you tell me a little bit about your relationship to Misa, and how that’s developed over the years?
As I got to know Misa and grew my relationship with her, she really just helped shape my career, seeing the things that I was good at, and seeing the things that I lacked. At the time, I was just like, “Why hip-hop? Why rappers? Why do I need to do these things when you know where my passion lies?” But in the past five years, I’ve been so appreciative of those conversations with her. Thank God she saw what I didn’t see. She pushed me in this direction because it’s really changed the trajectory of my career and my life, especially now being in a full circle moment, working with my first independent client that’s a female rapper. It’s great to be a part of Flo Milli’s legacy, then play on all the different lines of being girly and feminine and having those essential rapper attributes.
When you started your career, what were some of the hardest obstacles?
The most constant issue as a Black stylist with Black clients is sourcing. Until you’re at the height of your career, people don’t want to lend and support. We do get a lot of support from certain brands and I very much appreciate that, but there are other brands that we don’t get that support from. We have to just buy it, and if we don’t buy it, we won’t have it. Although we push the culture forward and we are the influence, they still don’t give us the same support and respect that they should. Because of that, since the pandemic, I’ve been fortunate enough with Flo to work specifically with brands that do support her and with Black-owned brands. We’re able to stay in that space, and it’s intentional, because they’ve supported us, so we want to continue to support them as everyone in the scenario grows.
As an aspiring stylist and an assistant, the thing that people maybe don’t pay attention to enough is how much time assisting takes. It takes going through some things; it takes really committing to being an assistant. To learn how to be a leader, you have to follow. It’s learning from people — good, bad or ugly — what you need to navigate in the industry: the skill set that you need, the work and determination that you need, the capital that you need. I think it looks so glamorous and it seems like such an incredible job. It’s not just artistic, it’s not just creative; at the base of it, it’s a business. So, it’s having the patience to wait until it is your time and up until that time being able to pour into somebody else’s career as an asset and help them while learning.
Vera Wang said it took her so long to start her company because she was assisting and she was being paid to learn. I look at the last 10 years of my career in a similar way. I was being paid to learn under some very incredible people, but I think it’s the humility that you probably don’t see.
Who are some clientele you would like to add to your roster? Where do you see yourself going next?
I would like to get more into the athlete space, and have both male and female clients. I’d love to have the gauge of being able to broaden my range. I love artists, but I think having too many artists can be a little tricky. I would like to do more creative direction, working with brands, and doing more design.
I was just the assistant costume designer for “Power Book II: Ghost,” the second season. That was an incredible opportunity and experience. I did that with Eric Archibald, so that was a cool eight months. I wouldn’t mind doing something else that is costume design — and that’s something else I love about Flo because she’s so multifaceted. She’s going into the acting space with her visuals, and it’s so great that we’re able to dabble in costume design, too.
Will you be joining Flo Milli on tour?
I’ll be there for the first 10 days.
What does tour prep look like for you as a stylist?
It’s intense. I’ve been on a lot of tours, though, so I’m fortunate enough to already have a base of it. You’re making sure that there’s a look for every city, then a fine line of giving her a range of options for when she wants to have options. But we’re still sticking to a costume and a silhouette so that her audience gets the same show every night. I think aesthetically it’s importantly to give the same costumes as well so that it feels the same and no one feels like they got a different experience.
You’ve talked about how you’ve wanted to maintain uniformity in the show, but is sourcing difficult because of the fact that it is a tour? Do you need multiples of a garment or are you constantly washing the same pieces?
Sometimes you do want to have something different for each date, but it’s not realistic. It doesn’t matter where you are in your career. What you’re supposed to do on tour as an artist is have a costume, so you should have costumes that interchange color palettes but then they get cleaned on your off days. Especially for Flo being her first tour, her breakout tour, so we’re just getting warmed up and just getting started. Once she gets to that larger space, we’ll really have all the surprises and the glitz and the glamour. But I think for this one, since she was a COVID artist, it’s important that she is able to connect with her fans and be comfortable and give a good show. She is Gen Z, she’s a real rapper and she likes to get in the audience.
Can you describe what we’ll expect from Flo Milli’s style on tour?
I wanna say her tagline [i.e., Flo Milli Shit!], but you’re gonna see talent, you’re gonna see artistry and you’re going to see vibrations. I think it’s important that it’s relatable. I personally get tired of seeing everything be so costumey and everything mirroring each other. I don’t like the fact that everyone looks the same, like all the female acts and artists seem to have one silhouette, all crystals. What you’re gonna see with Flo Milli is what I hope you’ve already seen, which is consistent with the Flo Milli aesthetic. You’re definitely gonna see the Flo Milli flip and you’re gonna see the elevation of her style, but it’s still gonna feel like Flo. It’s not gonna feel like a Broadway show. You’re coming to see her rap and that’s what you’re gonna get.