From Pop-Ups to Power Suits: An Evening with MM.LaFleur’s Founder
Last month, we welcomed a room full of retail dreamers, founders and fashion lovers to The Retail Playground IRL for a conversation with Sarah LaFleur, Founder and CEO of M.M. LaFleur. Hosted at their Chestnut Hill, MA location and moderated by yours truly, the evening was packed with style, substance, and the kind of inspiration that lingers long after the event ends.
From the start, Sarah brought a refreshing honesty to the conversation—pulling back the curtain on what it really looks like to build and lead a brand through major evolution. She spoke candidly about the rollercoaster moments of her founder journey, navigating major transitions (like her co-founder stepping away from the business), and the ever-elusive balance of entrepreneurial ambition and motherhood—calling parenting “the hardest job in the world,” a sentiment that resonated deeply with so many in the room, myself included.
What struck me most was how relatable and grounded Sarah is. She shared her take on “shiny object syndrome” and how, in a surprisingly comforting way, being constrained by budget and bandwidth can often be the best clarity-maker. It wasn’t just what she said—it was how she said it. Everyone was lingering on Sarah’s every word.
One of the most memorable moments came at the end of our conversation, when I asked Sarah to name the one item in her wardrobe that never fails to make her feel confident. Sarah’s answer? The O’Hara jacket. The kicker? I realized I was wearing that exact jacket at that very moment. A fun coincidence—and living proof that great design can be empowering. Let me tell ya, that piece really is a confidence booster ;)
It was an evening full of career reflections, community, and confidence—M.M.LaFleur style. And we were honored to host a space where emerging founders could see what’s possible, ask bold questions, and maybe even find their own O’Hara moment.
So, what did Sarah share? Let’s dive into the highlights that had the room laughing, taking notes, and feeling inspired.
“Women, on average, spend two more weeks per year getting ready than men.”
Sarah’s “WHY” was abundantly clear. She kicked things off by sharing the origin story of M.M.LaFleur—a brand born not from a business plan, but a personal frustration: being a busy professional with nothing to wear that truly felt great. She recalled mornings staring at her closet and feeling uninspired with a laundry pile full of dry-clean only and how that led her on a mission to create elevated, durable, beautifully made clothing that could stand up to real life.
“One of the things I’m most passionate about is great fabric…we’re really trying to create things that stand the test of time.”
We dug into our shared experience of growing up with entrepreneurial parents. Sarah’s mom started her own business out of their basement, importing American catalog goods to Japan and paving the way for what would later become a successful jewelry brand.
“I definitely have some vivid memories of what she went through…I remember thinking, ‘Wow, this looks hard.’ Entrepreneurship was not glamorous in those moments—but in a way, I think those experiences shaped how I approached my own business journey. I learned a lot from her, but it also gave me a realistic sense of what to expect and what I needed to be prepared for.”
DRESSING THE NATION (Literally)
One of the most moving moments came when Sarah recounted the launch of M.M.LaFleur’s ‘Ready to Run’ campaign, which aimed to dress women running for political office. Originally envisioned as a small gesture—"I thought maybe we’d dress 20 women"—it quickly ballooned into something far bigger, with over 1,200 applicants and a powerful mission.
Before Sarah knew it she had senators, congresswomen, and even Cynthia Nixon wearing M.M. LaFleur on the campaign trail.
“When we started, we had no idea it would blow up the way it did. But this woman, she wrote to us saying, ‘I’m a single mom living on the poverty line, running for state senate because it’s important for people like me to be heard. I would never be able to afford a blazer like this, so thank you.’ That moment really hit home. We were able to make a difference for women who otherwise couldn’t afford that kind of support, and that’s when I knew the campaign was more than just about clothing—it was about giving these women a voice.”
SARAH’S TAKE ON POP-UPS
For any emerging retail entrepreneur, Sarah had this solid piece of advice: “Do a trunk show or a pop-up…you need to get real, in-person feedback on your product. It doesn’t matter if your mom, sister, and friends say, ‘Oh, I love it, I love it…'“
“Until a complete stranger is willing to part with their hard-earned money, you won’t know if your product is good. That’s why pop-ups are so essential for testing products in real life.”
Although they currently have eight stores across the U.S, M.M. LaFleur’s journey began with pop-ups out of necessity, and Sarah still champions them as the best way to test a product and connect with real customers.
“IT CAME TO ME IN A DREAM”
When I asked about her most outrageous brand activation, Sarah described a dream-turned-reality: a full takeover of the iconic Russ + Daughters diner in NYC, complete with tap dancers in M.M. LaFleur’s latest collection and caviar on bagels. It was over-the-top, brilliant, and 100% on-brand.
That level of creativity comes with challenges, though. “I’m always the person saying, ‘We could do this and this and this,’ and my team’s like, ‘Here she goes again.’ But they and the numbers always bring me back down to earth.” I’m right there with ya Sarah—we have very similar dynamics at play over here too.
NAVIGATING CHANGE WITH GRACE
I closed the formal interview portion by asking Sarah about a recent major leadership transition. Her longtime Co-Founder and Creative Director, Miyako Nakamura had just stepped down, and M.M. LaFleur welcomed a new Creative Director to the team, Jennifer Coté.
“I just couldn't fathom doing it without her.” Sarah said candidly, “But I think that's where I had some honest conversations with myself where I was like, ‘I actually still have energy to keep going. I want to keep going. I love what I do. I've got another 10 years in me.“ And when asked about the transition from Miyako to Jenn, Sara replied that she thinks she’s “really honoring the DNA that Miyako put into the brand” and “bringing in her own flair, and I see it, and I love it!”
“Over our fourteen years of partnership, we built so many things together: a beautiful team, a brand we are both proud of, and a genuine friendship that will last forever, even if our business partnership dissolves.”
Read more about Sarah and Miyako’s “conscious uncoupling” here.
SARAH’S SPEED ROUND
Allison: Heels or flats?
Sarah: Flats. 100%. I'm wearing heels tonight for you, but I do want you to know these pants, they have snaps in them because when I wear them with my flats, I just snap the hem. All of our factories were like, "You're crazy." I know it sounds a little gimmicky, but it's the most convenient thing, so I don't choose between heels and flats.
Allison: If you could raid anyone’s closet, whose would it be?
Sarah: I would probably say that the closet I admire most is Cate Blanchett. I love her architectural style. I think she has an amazing stylist. I love it.
Allison: Are you a morning person or a night owl?
Sarah: Really neither. My kids are early risers, and so if I do want a quiet minute, then I have to set my alarm at a ridiculously early time. I hear about a lot of people, particularly entrepreneurs, who do that. They meditate and they journal and they do all of that, and I'm lucky if I do that like once a week, you know?
Allison: What’s one good book that you would recommend to every entrepreneur?
Sarah: Good to Great the obvious one, but the book I would actually recommend to every woman is called The Kingmaker. It is an unbelievable story about this woman, Pamela Herman, who was a U.S. Ambassador to France. She had to use both her feminine wiles and her intelligence to get as far as she did. And I was just like, "Wow, this is unbelievable."
Allison: What is one thing that people would be surprised to know about you?
Sarah: I’ve dealt with anxiety and depression for most of my adult life, which I try to be open about. I think I’ve overcome a lot, but it definitely peeks its head in every now and then. I think it's important to talk about.
Allison: If you weren’t in fashion, what would you be doing?
Sarah: I’d probably be doing something with the International Rescue Committee. We work very closely with them. It's one of the world’s largest humanitarian organizations. It's an amazing, amazing organization.
Allison: Favorite travel destination for fashion inspiration?
Sarah: Paris. I know that's so obvious. What I love about Paris fashion is that it’s not as expensive as people think. When people think Paris, they think expensive, expensive, expensive. But actually, they have beautiful niche brands at prices that are comparable to ours. It's a healthy middle, and it feels like you have more options than just H&M or Chanel. Sometimes in the U.S., it feels like there's not much of a middle.
MY BIGGEST TAKEAWAY
After the event, what struck me most wasn’t just how thoughtful and visionary Sarah is—but how real. She didn’t shy away from the hard stuff: partnership struggles, parenting while leading a company, the mental load of entrepreneurship. It was a reminder that behind every polished brand is a human being doing the work, making tough calls, and chasing big dreams.
Also? We need more tap dancers in retail. Just saying.
Feeling the FOMO? Watch the full interview right here.
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