A CEO who embraces her femininity, Molly Fienning has spent the last few years discovering what it means to live—and dress—for herself. See what pieces she's loving or scroll to read more about her journey as a business owner and ultra-stylish CEO.

Molly's wearing: JW ANDERSON Peplum Bustier Dress in Black; ALEXANDRE BIRMAN Sofia Satin Sandal 85 in Black; GIGI BURRIS Indre Bow in Black

Q: How would you describe your style?

A: My mom used to joke that, in preschool, I would only wear dresses and my little sister would only wear overalls. So I've always been sort of like a dresses & skirts girl. I like feminine, flirty things, and I like a little bit of a nipped in waist.


Q: What made you interested in entrepeneurship?

A: My childhood dream was to be a spy for the CIA, ironically. I studied computer science in college, and moved to DC to pursue a path in intelligence. I re-met a boy from college who I had known, but never dated, a couple years later. He was in the military. He was a fighter pilot for the Marine Corps, and we fell madly in love, and we were engaged in four months. We couldn't be passing ships in the night, so he proposed and I ended up moving to rural Mississippi where there weren’t tech jobs. So, that's actually how I ended up kind of becoming an entrepreneur—I realized I was going to be moving all over every 6 to 18 months, and I needed to do something I could take with me.

Being around a lot of aviators, you know, at squadrons, we came up with this idea for baby aviators, or, Babiators. That was my first big business. I've had a couple small businesses, but that was the first one that is still around today, 12 years, 13 years later. It's a great business. Our team really runs the day-to-day. We've sold about 6 million pairs of shades over the life of the business, and we’re in 3,500-4,000 retail doors.

A few years after that, when Fox, my eight-year-old, was a newborn, I had not had oysters and martinis for the nine months I was pregnant, and that was the only thing I craved. So, our first date was The Ordinary here in Charleston. I tried this hot sauce that the bartender brought out with the oysters. Geoff, my partner now at Red Clay, was in the kitchen of The Ordinary and created our original hot sauce to pair with oysters, and two weeks later I gave him money to kind of start the business. It was passive income because Babiators were still very much my primary job, and a couple years after that when Babiators didn’t need me, and I got inspired to sort of step in to help Geoff scale the day-to-day of Red Clay in 2018. We drove up to the headquarters of Fresh Market with a bottle and a PowerPoint deck and sat down with the category manager for Hot Sauce, and we were like, “Try it.” His name was Dwight. He was like, I'll take a chance. Let's do this. And so he was our first full retail rollout, all 150 doors or something like that at Fresh Market, and then we got Whole Foods South the following year, Publix, all doors the year after that, and the rest is history.

Molly's wearing: SEA Diana Taffeta Off Shoulder Top in Black; ISABEL MARANT Mills Skirt in Straw; THEODOSIA Pearl and Turquoise Drop Huggies in 14k Yellow Gold; KHAITE Marion Ankle Strap Wedge Sandal in Natural

Q: That is so cool. It kinda makes me want to cry!

A: Kinda makes me wanna cry too, but what I've learned is, the older I get, the more I realize we are all on this planet with a sole mission, and we have gifts that we need to lean into. Things that energize and light us up and feel like a flow state are our gifts and things that deplete us and make us procrastinate, or that we hate are the things that we should not be doing because they suck our light, they suck our energy. As a business owner, I had to learn what brings me light and puts me in a flow state, which is the big picture, early days, branding of a business. Who's the customer? What's the font? What's the color palette? The optimization, the running of the business, the margins, the numbers, the team management, it's not really my true passion. I like planting these seeds, and then stepping aside and enabling those great CEO operators to scale it. So, you know, it's been a really fun path, and I'm excited to keep going.


Q: How does your career impact your style?

A: Not at all. I'm not practical necessarily. When I grew up, my mom was one of the first women on Wall Street and literally in the first co-ed training program at Chase Bank. In those days, there were one or two women in a sea of men in suits, and they had to lean into this masculine vibe:pantsuits and suit outfits and sort of being masculine in the workforce. What I really embrace is that I can be feminine, I can be flirty, I can wear dresses, I can show a little cleavage, and that doesn't take away from me being a strong CEO or leader. I went to an all-girls school for 15 years, started by French nuns, and there was this very wonderful, feminine, kind of proper French woman who taught me French in sixth grade. She said, "The feminism movement in America was like, women need to be men. And French women always embraced that we are equal but different.”

Our strengths of sensuality and sexuality and femininity, we need to lean into that, not hide that. So, I really think as a female CEO, in a lot of different male dominated worlds, like grocery or tech, I realized I can show up and be as girly and as feminine as I want and that's my power. It's my superpower. It's not a weakness.

Molly's wearing: DRIES VAN NOTEN Taru Polo in Off White; ULLA JOHNSON Kiara Skirt in Espresso; KHAITE Marion Ankle Strap Wedge Sandal in Natural

Q: What would your advice be to women who are afraid to embrace their femininity or sensuality?

A: I love that question. I actually had a girlfriend say to me a few weeks ago, “I wanna be more sensual and I wanna dress that way. You kind of embrace who you are and dress that way, and I kinda wanna do that too.”

I was just like, “Do it!” So I think for me, it's all about authenticity and truth. And like, if your truth is to show a little leg, if your truth is to be a little bit more seductive with your fashion, great. If your truth is to be more tomboy with your fashion, great. If your truth is to wear all black and embrace something a little bit more New York minimalism, great. So I think when people are not living their truth, that's what feels inauthentic. That's what feels off there, because underneath is a different human, and they have to play these societal roles in fashion because they're trying to make others happy. Life is short. I just turned 44, and I think like the past couple years of my early 40s have been me realizing that life is so short, and we need to put ourselves first. Then, the light that that brings shines on everybody, and everybody gets excited about it. Fashion really is just an extension of our self-expression and our truth. It gets me really excited to ask myself, who am I? Not what are the trends telling me to be, or what do, you know, the people at church want me to wear. Who am I at my core, and how does that show up in my style?


Q: When did you first notice fashion?

A: My school K-12 was a uniform school, but in pre-K we could wear our own clothes. When I was three or four, my mom said I wore a party dress every day. She said, “I would take you home from Bloomingdale's and the first thing you would do after you'd get your afternoon snack would be putting on the party dress we just bought, then you’d sit on the couch and watch cartoons in your party dress.” She said I couldn’t help myself. Looking back, there’s that element, but I think in terms of being aware of fashion, it happened around middle school. In sixth grade, seventh grade, you just want to fit in, right? There was this clique of girls where we all had like, the L.L. Bean backpack, the Doc Martens, or the two or three moments, just because we wanted to do what everybody was doing. In eighth grade, I kind of stepped away from that. It was like, I don't want to be part of a pack; who am I separate from that? And I think that's where, at 14, 15 years old, in academics, in fashion, in friendships, it became about putting myself and my voice out there.

Molly's wearing: SIMKHAI Vallan Sleeveless Mini Dress in White; ALEXANDRE BIRMAN Clarita Bell Sandal in Golden

Molly's wearing: ISABEL MARANT Kapri Dress in Scarlet Red; ALEXANDRE BIRMAN Clarita Bell Sandal in Golden