HOW SHE BROKE THROUGH
FEATURING JUNE AMBROSE
By Laura Antonia Jordan
6 Minute Read
June Ambrose, photographed by Marsha Lebedev Bernstein for Danimás
The creative director, designer and advisor to luxury brands risked a stable career in finance to follow her passion.
‘I don't know what it's like to be still,’ says June Ambrose, who right now is sitting and sipping tea in her Manhattan home. It’s 9 am and yet her trademark big hat—today a hairy, navy “fedora, cowboy, little chapeau situation” by Esenshel —is already in place. To the untrained, executing this level of stylistic flair on a midweek morning would take a magician to pull off. For Ambrose—creative director, costume designer, influencer, to name but a few—she likely pulled her outfit together in five minutes flat.
Excellent time management skills are particularly advantageous for an accomplished multi-hyphenate entrepreneur and businesswoman who wears many professional hats. No stranger to working at peak capacity, Ambrose has a particularly packed schedule right now. In February, she launched her new shoe collection with Naturalizer, called Style-letics by June Ambrose. When we speak, she’s in the midst of the “marathon” that is New York Fashion Week.
Multi-hyphenate comes with many meanings, but in Ambrose’s case, what it really translates to is defining culture. In the 1990s, she became the first to style hip-hop and R&B artists like Missy Elliott and Jay Z; in 2021, she designed the first women’s basketball collection for Puma. “I consider myself somewhat of a disruptor… I walk to the beat of my own drum,” says Ambrose, who, at 54, is also a wife and a mom.
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Born in Antigua, Ambrose grew up in the Bronx and majored in performing arts. There was no established path for Ambrose to follow. She broke through her various creative fields due to her own bravery, confidence, entrepreneurial acumen, and vision. Her overarching message: don’t wait to be given permission. “I've created a space where people feel like [something] is possible, or they realize it’s okay to do things that don't align with what society has considered normal,” she says. “I don't conform.”
She never has. Ambrose paved the way for the overlap between R&B and hip-hop with fashion. She put Missy Elliott in a puffy trash bag suit for the music video for The Rain. She helped artists like Busta Rhymes and Mary J Blige craft their public persona. Clothes are more than just clothes, knows Ambrose. “Someone's image and likeness, and someone's person… is who we are and [how] we project ourselves to the world.”
“In the early years of my career, I didn't ask for permission. I just did it… I’m always asking myself, ‘What would young June do?’”
For Ambrose, style is also a form of costume. Hats have become her own signature; she owns around 30. Performing arts unlocked her talent for building character and crafting narrative, along with a professional skill set that’s useful in her ever-changing job remits. ‘In the performing arts, you are essentially an entrepreneur,” she says. “You're going on auditions, you're looking for that next job, you're constantly looking for that gig.”
It’s a formative realization; juggling multiple roles and responsibilities is a job in and of itself. Today, Ambrose divides her time between working remotely at home and working from the offices of her various roles. To achieve peak productivity, she wakes at 5:45 am and meditates for 30 minutes; she also went vegan eight years ago for “cognitive function.” Protecting her mind, body and energy is important. “Sleep plus healthy food is non-negotiable.” Her outfits, like her schedule, change depending on her mood or the company she’ll keep that day. The modern-day Ambrose is no lone wolf, and she loves collaborating; she has had seminal creative relationships with the likes of the legendary director Hype Williams and Jay Z, with whom she’s worked for decades.
Missy Elliott performs at the Victoria’s Secret 2025 fashion show; June Ambrose speaks at the United Nations Headquarters in 2024. Getty
Ambrose had an atypical career path. Her first job was actually in an investment bank. She was not only among the youngest members of staff, but she was also “one of maybe two people of color” in the company. Her three-year stint in finance offered her a solid foundation from which she grew. It might not have been the vocation she would ultimately pursue, but Ambrose has no regrets, saying her time at the bank was “the most important part” of her trajectory. The lesson? Career paths can be wiggly, but knowledge and expertise gained from a diverse range of roles can be advantageous.
One of the most valuable lessons she took from her time spent in the corporate world was, she says, “a sense of how important financial literacy was.” It’s something that creatives so often neglect or find themselves bamboozled by, and that women have historically been excluded from. In 1994, she took a punt on herself and established herself as a business. “I left at a time when I had enough financial stability in terms of some money put away,” she says. “I was able to live off that to go back into pursuing what I loved, which was being in the creative arts’.
It might seem risky to leave behind a stable role, take a leap of faith, and go it alone. Passion is fuel, but confidence is essential. For anyone thinking of striking out, ask yourself whether you have the conviction of both, which are vital to handle uncertainty while creating opportunities for yourself. “Was I scared? Yes, of course,” recalls Ambrose. “It took extreme bravery to leave.”
Attending the Off_White SS26 show with Mary J. Blige, Ciara, and Ellie the Elephant. Getty
Shortly after, Ambrose took on an internship at Uptown MCA Records marketing department—a good friend was working at the time, which gave her an in. She began working as a stylist, dressing the label’s talents for music videos.
Ambrose’s biggest asset at this time was her “childlike audacity.” It gave her the nerve to put herself forward for opportunities, ask to be given a shot; to try and risk failure. Decades later, she still tries to remain connected to that. She’s a brilliant advocate for the sensibility, “Why not me?” Women today have to fight so hard for equal opportunities within the workplace; it’s a beneficial mindset.
“I’m constantly asking myself, what would young June do?” she says. “In the early years of my career, I didn't ask for permission. I just did it. If I asked for the permission, I don't know if I would have been granted it, because it was something that had been somewhat unseen and untapped,” she says. “People are so afraid of the unknown that it stunts them creatively. So I stopped asking and started doing.”
That’s not to say everything came easy. Quite the opposite. We’re familiar with the advice to say yes to every opportunity, but Ambrose is an advocate for making the most of the no’s. Today, it’s normal to see Beyoncé and Jay Z front a Tiffany & Co. campaign, or A$AP Rocky shooting a short Chanel film. When Ambrose was at Uptown MCA, high fashion was largely uninterested in musicians, and especially hip-hop stars.
“One of the most valuable lessons she learned from the corporate world was the importance of financial literacy.”
Her solution? She showed those luxury houses what they were missing. She could see the possibilities of combining high fashion with street culture. Driven by conviction and artistic flair, Ambrose made the outfits for the music videos. “The imagery was provocative enough to shift the way people saw music in general.”
Today, she is a wise counsel. “Stop thinking about all the things that you cannot do,” she advises. “Think about ways of going around to get to where you need to go. Because if we're walking down the street and there's a pole in front of us, do we walk into the pole or do we go around it? There's always a way around something. You simply find the route.” She knows to trust her instincts, and has the confidence to do so. Cherishing her integrity, Ambrose says, ‘I try not to do things, [just] because the money is really good’.
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In 2020, Ambrose was appointed creative director of Puma, where she launched the brand’s first women’s basketball collection—a chronically underserved category. This was before the WNBA’s intergalactic popularity; before Caitlin Clark and A’ja Wilson turned women’s basketball into one of the most-watched games on U.S. TV. Ambrose was a woman, designing for women, in this particular sports space for the very first time.
She believes there is a power in outfitting no matter the industry. Outfits are a method of communication and a “language”. Clothes can “build confidence and make me feel seen in a world where you can disappear.” Her top tip for power dressing is to contextualise trends or garments with relation to yourself. “What does preppy or sporty or sexy look like for [you]?” she asks. “Take these headlines and interpret them in the way that [you] feel.” This way, “you wear the clothes; the clothes don’t wear you.” Dressing to feel like yourself guarantees success.
Once a boundary buster, always one. Does she like to scare herself? “I'm doing it now,” she laughs; her shoe collection is the latest example of that. The shoes—a mix of techy-strap sandals with ghillie-lace pointed pumps—are designed to serve a woman who wants to move with ease and feel sexy. It’s all about creating pieces that “cut through the noise.”
That’s not something that Ambrose worries about. Not now, nor has she ever. “Someone said to me the other day, ‘I find it so fascinating how you can exist and cut through the noise of a time when it's all about the young TikTokers and influencers, and still be of influence’”. Her response? Not to ever give in to the pitfalls of comparison. “I cannot compare myself or compete with those individuals. But can I exist? Can I be me, and can that be enough? Yes. It is.”
At the Glamour Women of the Year Awards in New York in 2024; Getty
The Tangible Takeaways: Ambrose's Professional 411
Time is precious. “What you put into something consistently reaps great reward.”
Learn from the no’s. Be prepared for the opportunities that didn’t work out; it doesn't mean that others won't come.
Be curious. “I still consider myself to be a student.”
Creativity is a muscle. “I'm constantly exercising it and working on it.”
Stop asking, start doing. Don’t wait for someone else to give you permission to try.
Be brazen, confident, and brave enough to try something that “feels so heavy to lift that it's too hard to obtain… Start at very low weight, and build and build.”
Know the numbers. Financial literacy is vital.
The Coffee Break Q&A
1. What’s the most important lesson you’ve learned in your career?
“If you don't believe something, the person that you're trying to sell it to won't believe it either. So you have to stand on your centre. And say things with conviction.”
2. What’s your best piece of entrepreneurial advice?
“It's a marathon, not a sprint. There will be good days and bad days but like with a stock, when it’s crashing, don't sell. If and when things don't work out, you don’t give up. As an entrepreneur, you have to be prepared for the things that you weren't granted. But that doesn't mean you're not worthy.”
3. What personal goals do you have this year?
“One, I want to make more time for myself. Secondly, I really want to build strength. I've lost mass, and for longevity, I must build more muscle. I need to commit to a routine because I'm a very sporadic fitness person!”
4. How does movement help you do your job?
“Everything about the job is so physical! But also, movement informs you on the importance of what a body needs. If I'm creating a product for consumers, and I don't know what it's like to live in it, then I can't do my job. You have to experience what it’s like to run down the street in those shoes.”
