Today we’d like to introduce you to Lindsay Cunningham.
Hi Lindsay, we’d love for you to start by introducing yourself.
Retail was actually my first job at 15—I’ve been fashion-obsessed since forever. Total black sheep of the family. No one else cared about clothes, and there I was styling outfits for algebra class. I studied business in college, worked at Saks right after graduation, and then—life did what life does—and I ended up in Wilmington, NC, working at the Monkee’s there.
Fast-forward a bit: I moved to Charleston with my husband and brand-new baby, and out of the blue, the Monkee’s franchise owner called and said, “You need a Monkee’s!” I didn’t even hesitate. A few months later, we opened our doors in 2018.
Then… COVID hit. I needed pieces in the store that women could actually wear in real life—on the couch, to the carpool line, maybe to wine delivery pickup—so I created Livro. It was easy, cute, affordable, and to my surprise, it flew.
From there, Livro kept growing, and in 2024, I launched Olivia by Livro—she’s Livro’s fashion-forward, high-end little sister. And now here we are!
We all face challenges, but looking back would you describe it as a relatively smooth road?
Is any road completely smooth? I’ve had MANY bumps along the way. I grew up the complete opposite as I live today, so I learned how to make things work and figure things out very young.
Opening the store was a dream, but I was still deep in startup debt when COVID hit. It felt like trying to keep a boutique afloat in quicksand. But if there’s one thing I’m good at, it’s a pivot. I don’t let roadblocks define the route—I just reroute. That’s when I launched Livro. Between that and some social media and marketing changes, the store started taking off in a whole new way. By the end of 2020, we were not only afloat—we were thriving. Debt-free and finally breathing.
Olivia by Livro, on the other hand… she’s a little more high-maintenance. Growth has been slower, but I’m learning to be patient with her. She’s still finding her place.
Thanks – so what else should our readers know about your work and what you’re currently focused on?
I run a high-end women’s boutique in Charleston called Monkee’s of Mount Pleasant, and I design two fashion lines: Livro, which is wearable, versatile, and easy to love—and Olivia by Livro, her more expensive, fashion-forward little sister.
My sweet spot is blending elevated style with approachability. I design and buy with real women in mind—moms, creatives, travelers, business owners—women who want to look pulled-together without trying too hard.
I’m most proud of building something from scratch that women actually wear. Not just once for a photo, but over and over. I love when someone tells me, “I’ve worn this dress a dozen times and still get compliments.” That’s the win.
What sets me apart? I have a very specific eye and a pulse on what will actually sell. I know my customer, because I am my customer—and I trust my gut. It’s a mix of intuition, grit, and a lot of Google Sheets.
If we knew you growing up, how would we have described you?
I was honestly a lot like I am now—independent, opinionated, scrappy, but full of life. I grew up with a single mom who worked constantly to provide, and a tough older brother who definitely kept me on my toes. We didn’t have much, but I always had big energy, big dreams, and zero interest in staying stuck in the life we had. I’ve been a hard worker for as long as I can remember.
That said, time (and motherhood) have softened me a bit. I’m still fiercely loyal, still a little feisty, but I’ve learned how to channel it. My childhood shaped me in all the best ways, and I’m incredibly grateful for it.
As for interests—fashion was always it. My grandmother (my favorite person in the world, still to this day) used to take me shopping. We’d raid the racks at Walmart and JC Penney like they were Bergdorf’s. I was obsessed with trends. I also loved interior design—I’d rearrange and redecorate my bedroom constantly. If I wasn’t styling myself, I was styling a space.
Contact Info:
- Website: monkeesmp.com | shoplivro.com | oliviabylivro.com
- Instagram: @monkeesmp, @shoplivro, @oliviabylivro
