In our long-running series, "How I'm Making It," we talk to people making a living in the fashion industry about how they broke in and found success.
About a week after I spoke with Jason Rembert about his trailblazing and headline-making career, Issa Rae walked the red carpet of the Critics' Choice Awards in a look that only he could create. One might assume that refers to the celebrity stylist's track record of fostering a strong visual identity among his clients or an appreciation for emerging design talent, but this look was even more personal than that. It was the premiere of Rembert's next professional endeavor: his own collection, Aliétte.
Inspired by the women in his life — likely including the "Insecure" actress who wore it, but more on that later — Aliétte's 2019 debut follows over a decade of unforgettable moments orchestrated by Rembert. For some perspective, that includes: Zayn Malik's robotic arm at the 2016 Met Gala; Solange's crystal-covered, braided-halo look for her "Cranes In The Sky" performance on "SNL"; Rae's all-Black-designer wardrobe she wore while hosting the CFDA Awards last year; Ezra Miller's Moncler x Pierpaolo Piccioli puffer gown at the "Fantastic Beasts: The Crimes of Grindelwald" premiere; Odell Beckham Jr.'s recent game-day style; and just about every impressive look from Rita Ora over the past seven years.
However, Rembert's appreciation for the unique and anti-status quo go back to before he was dressing celebrities. He credits his love of hip hop and obsession with Vibe magazine in the early aughts as his earliest forms of fashion education. And though he set out to pursue a career as a magazine editor, landing internships at Elle and W that got him in the door, it was his internship with industry veteran Wouri Vice that shifted Rembert's focus toward styling and the possibility of how he can interpret fashion.
"As a fan of hip hop, R&B and of my culture, it was amazing to see that Wouri was able to get these high end brands that W and Elle and Harper's Bazaar were shooting and he was able to make it his own," says Rembert of his time with Wouri when he was styling Alicia Keys. This example not only influences Rembert's own career today, but also set him on a track to champion up-and-coming designers in his work — Shanel, Pyer Moss and Marc Keiser are a few current favorites — and become a mentor for the next generation of stylists who will change industry-wide perceptions.
Ahead of his latest career shift and, about two straight months of work for awards season and fashion month ("I don’t see a day off on my calendar until March," the stylist says calmly), we spoke with Rembert about how he became one of the most prominent and thought-provoking stylists for A-list celebrities and emerging talent alike. These are the highlights of our talk.
What were some of your earliest memories of becoming interested in fashion?
My brother was big into hip hop artists such as Jay Z and Fabolous who were wearing a lot of fashion-forward, luxury items. We grew up in an impoverished neighborhood and we didn't know much about luxury brands, so when these rappers said a brand in a song, that's when we were able to learn. As I grew, I started looking at Vibe magazine and there were editors such as John Moore and Memsor Kamarake who were styling these big brands that I heard in songs, like Christian Dior, Christian LaCroix, Margiela or Louis Vuitton. They were making it relatable to kids growing up in my neighborhood — I'm sure to all urban youth kids. You would see a full Margiela look and you didn't understand the intricacies or the aesthetic of Margiela, but by Memsor or John styling it with Nikes, or styling a Dior couture gown with bamboo earrings, you were able to relate to it.
When did fashion become a professional goal for you?
I went to college and was often applauded for my fashion. That was during the time of Ugg boots and Juicy Couture sweatsuits and, for me, I wanted to express myself more. After time, I realized maybe this is not the only setting for me so I decided to apply for internships. The first internship I applied for was Vibe and I didn't get the internship; I applied the next semester, and I didn't get the internship. I got frustrated but determined. After hours of searching, I found this site called Ed2010.com; it was like 3 o'clock in the morning and I was going through internships and I stumbled upon Elle. At that time, I didn't know what was inside the magazine, but I applied. I woke up the next morning and I had a reply and they asked me if I could come in. I met with about five fashion assistants within an hour of my interview and by the time I took the train all the way back to Long Island to my dorm room from the city, they hired me.
After your internship experience, how did you find your way to celebrity styling?
After Elle, I went to working at W in the fashion closet. I built relationships and there was an opportunity to intern for a celebrity stylist named Wouri Vice. He was styling Alicia Keys at the time and the first job was Alicia's album packaging. Instead of how a magazine editor would have to shoot full looks, Wouri was able to bring back that excitement that I got from Vibe and make it relatable to me or relatable to Alicia's audience. That was the first time I fell in love with celebrity styling and knew it was more of my calling than being a fashion editor.
Once you decided to make the shift, what was it like securing clients in the beginning?
My first client was during my W internship. June Ambrose was looking for three stylists for BET's "Rip The Runway" and the day I was supposed to interview was the day I had to work at W, so I went on my lunch break. It was probably 10 blocks away but at that time I didn't have any money, so I had to walk there and back. I was in trouble for being late but I got the position with BET "Rip the Runway." It was with a girl group called Electrik Red and they ended up becoming my client after the show.
You and Rita Ora have been working together for seven years now. How did that relationship get started?
I got an agent through one of my closest friends; she was a bartender at a really popular restaurant in the city. I couldn't afford food so she'd let me come to the restaurant and sit at the bar and get free food. There was a guy who was a regular and and his best friend owned an agency for stylists, so my friend connected us. I became a stylist with the agency and started working with small clients like Jeremih, Range and Nicki Minaj when she was new.
After two years with the agency, I got a call that there was a new artist they wanted me to work with: ASAP Rocky. I ended up doing a video with ASAP Rocky and on the set for the video, I'm walking out of the trailer and they called again and said they'd like me to work with another new artist: Rita Ora. ASAP Rocky didn't end up working but Rita did.
What was the point in your career when you felt like you were beginning to hit your stride?
When I first started working with Rita, I was requesting clothes and no one would lend to her. Then as she grew and she became more of a fashion girl, she was getting big brands such as Chanel and Tom Ford, and we got invited to the Met Gala. I think my career changed then.
What is the biggest challenge when it comes to advocating for your clients to the brands you're working with?
Being transparent with brands and making sure to hold brands accountable to be transparent with me. There are a million brands, so if a brand says no to my client or to one of my projects, I don't really take it personal at all. I would just love the transparency from both sides. I will let the brand know in the fitting why it didn't work and if it could work for the future. Not every person works for every brand and not every brand works for every person.
What kind of discussions are important to have when bringing on a potential client?
Communication is key. I want to hear where they see their style and where they see their style going. I also like to ask my client what brands they're currently into and what brands are inspiring them. From there, I reach out to brands and I do my best to build relationships. In this industry, some people think things will happen for them overnight, but for the most part it's very political and each carpet means something — if it's a big brand, if it's a new brand, if it's a brand that's more artistic — and it has to match with what you're putting out there for that current campaign. When it's constant, it looks to the world like you have a clear identity. People want to buy into things that are genuine.
How do you ensure your work remains genuine?
I'm definitely a person who's out there for what's next. I'm going to go hard on being the first to discover a brand. I'm up at three or four o'clock in the morning on Vogue Runway and Instagram; I'm looking for what's next and reaching out to these people through email and DM. I just want my clients to be aligned with authenticity. I'm not going to put my client in a huge brand with a look that I don't believe in, just because of the brand. I want my clients to have identity and I want them to have depth to what they're putting out in the world — what I'm putting out there in the world.
You've had a few huge press moments this past year for your work, like Ezra Miller's "Fantastic Beasts" press tour or Issa Rae's CFDA Awards looks; what were the moments that stood out for you?
Those were the two big ones for me that were extremely important. Ezra is definitely a person who had a clear aesthetic on who he is, and for me just to be a part of it and help him and collaborate to get to the point in his career, I'm totally grateful for. And Issa, she's one of the realest people I know. She is a visionary, she is strong, she is beautiful and what she's doing for culture as a whole is something that inspires me daily. When I brought the idea to her about wearing Black designers, she was all in. And she wanted to be clear that she wanted to do it in its entirety — even with the accessories, they were Black designers. It was amazing for have someone who is willing to take the risks wearing smaller designers when every huge designer wanted to dress her for the CFDA Awards.
What do you think is the biggest difference in your career today from when you first broke into this business?
Celebrity style is different in that it's more popular. I get a lot of emails and DMs from kids wanting to become stylists or wanting me to be their mentor and I find that to be amazing. When I first started there weren't any Black or minority stylists in Hollywood, and to see these kids aspiring to be me — or Law Roach, Ade Samuel, Wayman and Micah, Jason Bolden — it's like, this is the future. I'm hoping these kids become as great as I am or even way higher, because it's going to be able to change the future.
What's important advice you think those who are following in your footsteps should know?
Work hard. Humble yourself. Intern. Assist. Do test shoots. Work with anyone and everyone. Build relationships that are true. As a stylist, figure out who you are and what inspires you. And once you figure it out, go after it.
What have you learned about managing your own time when you're so often working on the schedule of so many different and high-profile clients?
I sacrifice so much with those kind of things. I sacrifice family birthdays, my birthday, but the good thing is that I have balance. I have a very supportive family and I try to always fly back to take my son to school or spend time with my daughter. If I'm in New York, I'm usually working from home so that I can maximize the time I'm spending with them and that's really it.
Do you think these sacrifices are just par for the course in this line of work?
I think in any industry that you work there are going to be sacrifices. Do I enjoy a day off? Yes. Do I enjoy laying on the couch and watching "Law and Order?" Yes. But there are so many more things I want to accomplish that I feel like if I sacrifice now, I'll be able to do all those things, plus more, in my 40s. But I'm not saying everyone should sacrifice at all; it's my choice.
You just debuted the first design from your own collection, Alliéte. In what ways does this feel like the next natural step in your career?
In 2018, I thought long and hard about debuting a collection. I knew I wanted to be women's, as I'm inspired by all of the women in my life. The brand Aliétte is named after the two women that had the largest impact on my life thus far: My late mother Louisanne Aliétte and my daughter Harper Aliétte. The debut collection is based off Martinique, the island from where much of my family comes. As a kid, my mother told me many stories about the Island, and after her passing I kept her passport with all of her travels to Martinique.
What's the biggest professional challenge you find yourself facing right now?
My biggest challenge is just time and having enough time for the clients I take on. I try not to take on too many more projects than I can actually handle with my team because I wouldn't have direct communication with every single one of my clients. I don't want my clients to ever feel that I'm not there or that one client's project means more to me than another, because they all mean the same to me.
This interview has been edited and condensed for clarity.