Let’s start at the beginning. What was your childhood like?
Looking back, one of the biggest influences on me was being a gymnast. It taught me discipline, focus, and resilience. I also grew up in a small, homogeneous town where I always felt a little different. I felt there was a bigger world out there and wanted to see more, do more, and build something of my own. The other major influence was growing up around fabric, lace, and design. My family had been in the lace business for generations and was one of the largest lace manufacturers in the country. I loved visiting my dad’s office, walking through the factories, and watching beautiful materials come to life.
Did those origins shape who you are today?
At the time, I didn’t realize how much I was learning, but it gave me a lifelong appreciation for craftsmanship and creativity. Even as a kid, I was making clothes for my Barbie dolls and decorating dollhouses with fabric scraps. Then I went to Penn and thought success meant banking or law. My dad would always tell me, “You’re so creative—do something creative.” What started as a hobby—making bags, capes, and eventually pants—turned into a business. Did I know I’d build a global brand? Absolutely not. I just loved creating beautiful things.
For the OG Alice + Olivia customers, the brand started with one mission—creating the perfect pair of pants. How did that idea come about?
It was the height of the denim era, and I felt there was a gap in a woman’s wardrobe. I wanted to create a pant that had the comfort and fit of a great jean but felt more elevated and fashion-forward. For the first year and a half, that’s all we made.
This year marks 25 years of Alice + Olivia. What are you most proud of?
The culture we’ve created. The teams we’ve built. What the brand represents to women. I’ve never seen someone put on our clothes and not smile. Whether it’s our suiting, our prints, our dresses, or our colors, there’s joy in it. We even hide little positive affirmations inside our jackets and button-downs. Things like “You got this,” “Go for it,” and “You look good.” Sometimes people don’t even realize they’re there.
Were there ever moments when you doubted whether the business would succeed?
During the pandemic, absolutely. There was definitely a moment where I thought, “Oh, my God, are we going to survive this era of sweatpants?” We made party dresses and colorful suiting. It was terrifying. But as a leader—and especially having my husband, Andrew, by my side—you learn to stay calm and keep moving through the storm.
Over the years, you’ve become as recognizable as the brand itself. Was that on purpose?
Not really. I think it happened naturally. Today, people want to know the person behind the brand. They want to see how things are made, why they’re made, and what happens behind the scenes. I always try to make anything I do publicly about the clothes and the brand, but people connect with authenticity. They want to understand the process, whether it’s design, digital innovation, or fit development. Sharing that journey has become really important.
How is the Stacey Bendet of today different from the woman who launched Alice + Olivia in 2002?
Well, for one thing, I’m not Rollerblading to work anymore.
Why not?
We’ve evolved a little. I’ve grown up. The brand has grown up. We’ve become more sophisticated, but I hope the inner child and the whimsy are still there.
Your signature eye makeup is almost as recognizable as your designs. Has that look evolved over time?
Definitely. There’s a version of me that’s completely makeup-free: vegan yogi, hair in a messy bun, full Hamptons mode. Then there’s the black eye makeup look. Sometimes it’s more gold, sometimes more black, more sparkly, more cat-eye. It’s evolved over the years. I always say nobody is just one thing. We all have different versions of ourselves.
You’ve also been open about your beauty treatments.
I think there’s such a stigma around women wanting to look younger or improve something about themselves. My attitude is, if something bothers you and you can safely change it, why not? When I shared my baby lift, I received thousands of messages. Some people asked why I did it. Others thanked me for being honest. I think women appreciate transparency. If something worked for me and made me feel better, I’m happy to share it. We’re living through a beauty revolution. There are so many incredible technologies and treatments available now. At the end of the day, I just like making things beautiful, whether that’s fitting a pair of pants or improving my skin. It’s all aesthetic to me. It’s about being your best, doing your best, and feeling your best. We always say, “Look good, feel good, do good.”
Is there a treatment on your beauty bucket list?
Right now, I’m interested in biostimulants. There are stem cell–based options, peptides, polynucleotides—so many fascinating innovations. My dermatologist and I created a protocol we call “Stace Face.” It’s a combination of microneedling with ingredients like polynucleotides, tranexamic acid, Botox, and hyaluronic acid. It makes your skin incredibly glowy. I also love SoftWave [Tissue Regeneration] and Pico-toning for texture, tightening, and pores.
Why do you think your brand resonates with both legacy customers and the next generation?
That’s such a compliment. Women of my generation grew up wearing our clothes, and I hope younger women are inspired by what we’ve built. My daughters wear our jeans and tops. My mom and mother-in-law wear our beaded jackets, sweaters, and blouses. I think our use of color, print, and fit appeals across generations. Nothing makes me happier than seeing a mother and daughter shopping together.
Would any of your kids join the business someday?
My daughter Scarlett has incredible taste. She’s actually working on a project in my office this summer. She’s reimagining our Big Feelings sweatshirt initiative and renaming it Little Sister—like Alice + Olivia’s little sister. The designs she’s created are amazing, and she wants the project to support mental-health awareness. I’ve been impressed.
You have such a strong community of women around you. Who inspires you?
Nicky Hilton and Paris Hilton have been muses since we were about 20 years old. They’re iconic, elegant, and always inspire me with the way they wear clothes. I also love dressing Kathy Hilton and her daughter-in-law, Tessa. And honestly, one of the most iconic women of our time is Lauren Sánchez. The way she uses her voice, supports charities, advocates for neurodiversity and dyslexia, and embraces who she is—I think that’s incredibly powerful. Sometimes the women who inspire me most aren’t celebrities at all. They’re doctors, leaders, and entrepreneurs who are doing extraordinary things while wearing our clothes.
Let’s talk Hamptons. What does a perfect summer day look like for you?
This summer I’ll probably be out there more than ever. My kids are older now and want to spend time with their friends in the Hamptons. I love doing yoga, taking long walks, going out on boats, waterskiing with my kids, playing pickleball, and stopping by our stores. I’m obsessed with those tiny Hedley Studios electric sports cars and desperately want one to drive around this summer. I also love Sag Harbor dinners, farmer’s markets, and random vintage shopping.
Do locals recognize you when you’re walking around town?
They do, but I’m pretty used to it.
What’s something people assume about you that’s completely wrong?
I think people sometimes assume fashion is all glamour. I work my ass off. I’m in meetings from seven in the morning until six at night. I’m deeply involved in every part of the business—not just the clothes, but the operations, strategy, and growth. Instagram looks fabulous, but I’m in the office every day.
What’s your daily ritual?
Ashtanga yoga every morning. Nonnegotiable. And when I need to clear my head, I take long walks.
I’ve only ever seen you in sky-high heels. What are you actually walking in?
Honestly, sometimes I walk in the heels. But I also love a chic Louis Vuitton slip-on with a platform sole, Louis Vuitton sneakers, Prada’s suede Birkenstocks, and Roger Vivier sneakers with crystal details.
Is there a side of you people don’t get to see?
People don’t always realize how much I love business and science. I’m obsessed with learning about AI right now and figuring out how to apply it throughout our company. I also love longevity science—stem cells, polynucleotides, cellular regeneration. I could talk about that stuff all day.
What does having an impact mean to you?
I’m still growing the business. I want to launch fragrance, lingerie, and entirely new categories. But I’m also thinking a lot about legacy. One project we’re exploring is helping create a fashion business major at NYU. There are amazing design schools, but not enough programs focused on the future business of fashion—AI, robotics, technology, and entrepreneurship. For me, it’s about continuing to create, learn, grow, and contribute.
So Professor Bendet could be in your future?
I don’t know if I have the attention span for that. [Laughs] But helping build a program like that? Absolutely. Supporting the next generation of fashion business talent feels incredibly important.
Many of your friends have been on reality TV. Have you ever considered it?
Honestly, I don’t even think people would believe the reality show. I’m not sure I’m ready for that, but let’s just say there’s never a dull moment. I may be a lot of things, but boring isn’t one of them.
Do you intentionally keep your personal life more private?
I do, but trust me—it’s not boring.
At this stage of life, what feels most important to you?
Family. Always. My work and my teams are incredibly important to me, but every day I’m a mom first and a designer and CEO second. What’s really special now is that my kids are getting older and genuinely proud of what I’ve built. That means everything.
Sydney Sadick
