June Ambrose's World: Her Fearless Style, Her Defining Career Moments, and the Lessons She's Passing Down to Her Daughter

Step into the universe of the coolest creatives in the fashion industry with our series My World, where readers will discover how the top stylists, designers, and tastemakers built their careers; their favorite restaurants, beloved albums, and fashion finds; etiquette rules they stand by; and so much more.

There's a quiet authority June Ambrose carries. Not everyone knows that she is the name behind many iconic red carpet, music video, and celebrity style moments, but fashion-industry insiders are well aware. The legendary stylist, costume designer, and creative director has entered a chapter defined less by proximity to power and more by intention. It's a level of clarity that only comes with the knowledge, experience, and self-trust she's earned over the years in this industry.

For Ambrose, success has never been about doing everything at once. It's about discernment—knowing when to lean into work, when to protect her energy, and when to prioritize family. "Work/life balance is a constant balancing act, not a fixed formula," she explains. "Different seasons require different priorities, and that's okay." That philosophy extends to her most recent project, a collaboration with Naturalizer that challenges the long-standing trade-off between comfort and style. Rooted in what she calls Style-letics, the collection fuses fashion, movement, and culture and is designed for women who live in multiple modes and refuse to shrink themselves into just one box.

Her world is one shaped by fearless style and deep intention, informed by icons like Grace Jones and Donna Summer, and guided by a belief that fashion is communication. It's also deeply personal, and this current era of individuality-first style was made for her. From the career lessons she's passing down to her daughter to the pieces in her closet she hopes will one day become heirlooms, Ambrose's approach to style—and life—is about legacy, not noise. Ahead, she opens up about the creative instincts that define her, the moments that shaped her career, and why true power should always feel like freedom.

Tell me what work/life balance looks like to you. How do you juggle family, yourself, and having a successful career?

I stay grounded by being intentional with my time, protecting my energy, and knowing when to lean into work and when to lean into family or myself. Creativity thrives when my life feels full, not depleted.

To me, real success isn't doing everything at once. It's building a career that works with your life, not against it. Balance is grace, flexibility, and giving yourself permission to define success on your own terms.

How do you want to define your 2026 era?

Power with purpose.

My 2026 era is about intentional power—moving with clarity, confidence, and purpose. It's a season of refinement, where I'm expanding into new categories and aligning with partners who truly understand my vision and values.

It's less about doing more and more about doing what matters—designing work and a life that feels strong, elevated, and sustainable.

What project that you've worked on recently do you want us to know about?

Honestly, this Naturalizer collaboration feels like the most sincere work I've done in a long time. I wasn't interested in creating another shoe moment. I wanted to challenge a mindset. Naturalizer already spoke fluent comfort. They've been doing that for nearly 100 years. I came in to remix it, to push it louder, faster, further through my lens of high-fashion, street, and music culture.

This project is about saying something very clearly: Comfort isn't a bonus anymore. It's the baseline. Uncomfortable shoes are just rude, and women are done negotiating with pain in the name of style. This collection is fashion that understands movement. It moves like sport, looks like fashion, and feels like a revelation.

What served as the inspiration behind this collection?

The inspiration was real life. Women don't live in one lane. We exist in multiple modes all at once. Every day is a sport, yet our shoes have been stuck choosing sides for too long.

I call this idea Style-letics. It's the new choreography of fashion—the fusion of culture, movement, and identity. These aren't dress shoes pretending to be athletic. They're fashion pieces that understand how women actually move through the world. We brought performance-level cushioning into silhouettes you wouldn't expect because style shouldn't fight you. It should flex with you.

And I love that this conversation is multigenerational. My daughter and I can wear the same styles differently, authentically. That's the future. Comfort as a birthright. Style with permission.

Describe the dream woman you want to slip into these shoes.

I always start with the woman: where she's going, what she's doing, and how she wants to feel when she shows up. These shoes are for women who can lead a meeting, walk 10 blocks, dance all night, and still want to make a statement without saying a word.

She doesn't apologize for herself, and neither should her shoes. She understands that style doesn't have to hurt to be powerful. Every shoe in this collection is a punctuation mark. It helps tell her story. Whether she's 25 or 55, she's moving through life with intention, confidence, and momentum. These shoes meet her there.

What was your first job in fashion?

It was as a costume designer for a musician. I don't really think my time in theater doing period pieces would count as fashion, but now that I write that, one would say that Donna Karan's draping was inspired by Greek gods. Antigone was my first.

What look that you styled are you most proud of?

I would have to say it was a look that I designed for Missy Elliott—the infamous shiny blow-up suit for her "The Rain" music video It was the beginning of me playing with augmented reality before AI.

What's something you wish you knew at the beginning of your career?

I wish I knew that my point of view was the product, not my proximity to power.

Do you have any mantras right now in relation to personal or career development?

My mantra right now is,

"Style is communication.

"Clarity is my superpower.

"My instincts are informed by experience.

"Taste is intelligence.

"Consistency builds trust. Intention builds legacy."

What advice do you give your daughter in the career space?

I tell my daughter to build herself before she builds a career. I want her to know that her voice, her values, and her boundaries matter just as much as her talent. Skills can be taught. Character, discernment, and self-trust are built. I remind her that she doesn't have to rush to prove anything. Timing is part of strategy.

Define your personal style right now in three words.

Sporty, sophisticated, fearless.

Where does your incredible sense of style come from?

My sense of style comes from my love of image-making and storytelling. I've always approached fashion as a way to build characters and create narratives using clothes to express mood, power, humor, and identity. Style, for me, isn't just about what you wear; it's about the story you're telling before you even speak.

Are there any fashion icons that you've always looked up to?

Donna Summer didn't just define disco. She created a visual language of confidence, sensuality, and liberation.

Yayoi Kusama: art, fashion, and self-image as immersive culture.

Megan Rapinoe—androgyny, confidence, and cultural defiance.

Venus Williams pioneered style freedom in women's tennis.

Grace Jones shattered gender norms and defined power dressing with a future-forward edge that still informs fashion, sport, and performance culture.

Jane Birkin created a timeless language of ease, proving that authenticity, simplicity, and sensuality never go out of style.

Lauren Hutton changed the idea of perfection, introducing ease, individuality, and confidence as the ultimate luxury.

How has your style evolved since the beginning of your career?

My style has evolved the same way I have—through growth, confidence, and self-trust. Early in my career, style was about making a statement and commanding attention. Now, it's about clarity and intention, knowing exactly who I am and dressing in a way that reflects that without explanation.

Today, my style is more refined but still fearless. I'm less interested in trends and more focused on timeless pieces that move with my life. It's still expressive, still playful, still rule breaking—but grounded in experience, freedom, and a deeper understanding of my own power.

Is there anything you're still wearing that you've had since day one?

Yes, a Gucci pinstripe suit, big glasses, Birkins, and a Barry Kieselstein-Cord alligator belt.

Do you have a least favorite fashion trend?

I don't really believe in least favorite trends. I believe in misalignment. Anything that asks women to shrink themselves, sacrifice comfort, or dress for approval instead of self-expression isn't for me. Style should feel empowering and authentic. If it doesn't feel like you, it's okay to leave it behind.

If you could trade closets with one celebrity just for a day, living or dead, who would it be?

Teyana Taylor.

What was your first statement-making hat, and how did you become known for this iconic accessory?

Wow, that's a tough one. I've been wearing hats for so long, but I did fall in love with Stephen Jones's avant-garde hats years ago.

If someone is looking to expand their hat collection, where would you suggest they go first?

I love hats from Esenshel, Eric Javits, Eugenia Kim, and Gigi Burris.

How do you store all of your fabulous hats?

I build additional storage cabinets for them in my home and hat boxes in storage.

What's one piece in your closet you'd like to pass down to your daughter some day?

One of my Hermès Kelly bags.

Where is your safe space?

Home.

What was the experience like finding your current home?

I've lived in the same condo building for 28 years, so I didn't have to look far when I wanted a bigger place.

You travel often for work. What's the one hotel that feels like a home away from home?

L'Ermitage Hotel in Beverly Hills.

What's your favorite restaurant in your home city?

ABCV [in New York City].

If you could get a vacation home anywhere in the world, where would it be?

Antigua, my birthplace.

What does the perfect workspace look like to you?

My perfect workspace is calm, curated, and purposeful.

I like a mix of beauty and function—art that tells a story, books that hold history, textures that feel lived-in. The space has to reflect where I've been and where I'm going. It should feel elevated but human, polished but warm.

Who is an artist you know personally who you actually listen to nonstop?

Beyoncé.

Are there any binge-worthy shows you haven't been able to stop watching lately?

The Pitt.

Is there something in your queue that you're looking forward to watching, reading, or listening to that you haven't gotten to yet?

I also have the Battle of Versailles documentary queued up.

I've been meaning to revisit archival runway films, specifically Yohji Yamamoto, Comme des Garçons, early Jean Paul Gaultier.

Where do you gather inspiration from when it comes to the work that you do?

My inspiration comes from real life—always. I pay attention to how people move through the world. Style on the street, body language, how confidence shows up before words do. Culture tells you everything if you're willing to observe and dream with your eyes open.

Any good reads?

Grace: A Memoir by Grace Coddington

The Creative Act by Rick Rubin

Are any fashion trends from 2025 that are canceled?

Ripped skinny jeans, tie-dye.

What's the best way to spend a Valentine's Day single?

Gals' night out!

What's one styling rule that everyone should abide by?

Fit is nonnegotiable. You can wear the simplest pieces in the world, but if they don't fit your body, your lifestyle, and the moment you're walking into, the look won't land. Tailoring, proportion, and intention matter more than labels or trends.

What's your love language?

I respond deeply to acts of care—someone anticipating a need, creating ease, or holding space without being asked. That tells me I'm seen.

At this stage of my life, love looks like consistency, consideration, and calm. Loud gestures fade. Presence lasts.

What's something that's overrated and something that's underrated?

Overrated: being everywhere.

Underrated: being consistent.

What's the best gift for you to give and to receive?

To give: thoughtfulness. Something chosen with care—an experience, a book, a note, anything that says, "I see you."

To receive: time and presence. Undivided attention, follow-through, and effort, that's the real luxury.

What do you want people to take away from an interaction with you?

I want people to walk away feeling my authentic intelligence, that curiosity, intuition, and lived experience are my superpower.

Shop June Ambrose's Naturalizer Collection