Today we’d like to introduce you to Brittany Cobb.
Hi Brittany, so excited to have you with us today. What can you tell us about your story?
I’ve always loved the hunt.
Long before I built Flea Style, I was the kid wandering through antique malls and open-air flea markets in California, captivated by the stories hiding inside old things. I loved finding something unexpected—something with history, personality and a point of view. To me, flea markets were never just about shopping; they were about discovery, storytelling and finding something that felt entirely your own.
That feeling followed me into my early twenties living in Dallas while a student at SMU and when I moved to New York and immersed myself in the city’s legendary flea market scene. When I returned to Dallas for my dream job as a lifestyle journalist, I saw an opportunity to bring that same sense of discovery and individuality to a city craving unique shopping experiences.
So I started a flea market.
At the time, it was simply a side project. I had little capital and no grand business plan, but I had a background in storytelling, a deep love of vintage and a belief that people were craving something different. I launched The Dallas Flea while continuing my career in journalism, never imagining it would become the company I would build my life around.
But people showed up. And they kept showing up.
The Dallas Flea evolved into Flea Style, a lifestyle brand designed around my belief that style should feel personal, unexpected and fun. What began as a weekend side hustle grew into a multimillion-dollar business spanning retail, events, hospitality and experiences.
In 2021, we launched The Original Hat Bar, turning the simple act of buying a hat into an experience. Customers could shape, customize and personalize their own hats, making each one feel uniquely theirs. It became a natural extension of what I had always believed: the best style is the style you help create.
That philosophy eventually led us into hospitality with Heirloom Haul, our café and tearoom concept inside select Flea Style locations. Every part of the brand is designed to give people a chance to discover, connect and leave with a story of their own.
Hats have become one of the most meaningful parts of that story. I’ve always believed a hat can be more than an accessory—it can change how you carry yourself, give you confidence and become part of your identity. My own lifelong relationship with hats, along with my experience navigating melasma, has made that belief deeply personal.
Now, nearly two decades after starting The Dallas Flea, I’m putting those ideas into words with How to Style a Hat. Part style guide, part encouragement and part love letter to the hat, the book is ultimately about dressing for yourself, embracing what makes you different and finding confidence in your own point of view.
When I look back, it’s funny to think that so much of my life grew out of a love for flea markets. But maybe it makes perfect sense. I’ve always been drawn to things with a story—and to the unexpected discoveries that become the things you treasure most.
The business has grown far beyond the flea market I started all those years ago, but the heart of it hasn’t changed. I’m still chasing that feeling: the unexpected discovery, the perfect find and that moment when something feels like it was meant to be yours.
We all face challenges, but looking back would you describe it as a relatively smooth road?
Of course, building a business for nearly two decades has rarely been a straight line. There have been fires and floods that forced us to rebuild stores from the ground up, tariffs that changed the economics of our business overnight, copycats that challenged us to protect what we had created, and plenty of growing pains that came with scaling something I started so organically.
The truth is, there’s a new challenge almost every day. Running a business means constantly solving problems you didn’t know you were going to have. But I’ve never expected the road to be easy, and I’ve never let the bumps stop me in my tracks. I’m too passionate about what we’re building—and too curious about where it can go.
If anything, the hardest moments have often been the most valuable. They’ve forced me to become a better leader, make tougher decisions, get more creative and look at the business through a different lens. Sometimes the lesson is painful, sometimes it’s expensive, and sometimes it takes a while to see the silver lining. But there almost always is one.
I’ve learned that resilience isn’t about avoiding the hard things. It’s about moving through them, learning from them and using what you learn to build something stronger. Every challenge has shaped me as an entrepreneur and, in turn, shaped Flea Style. And after all these years, I’m still just as curious about what’s around the next corner.
Appreciate you sharing that. What else should we know about what you do?
One of the things I’m most proud of is that I’ve never had to leave the creative side of myself behind to become a CEO. If anything, running the business has given me more ways to use it.
I help design all of our hats, creating styles that are unique and exclusive to Flea Style. I’m constantly thinking about shape, color, proportion and the little details that make a piece feel special. Our stores are another creative outlet. With a background in interior design, I’ve always approached our spaces less like traditional retail stores and more like homes—layered, personal, collected and a little unexpected. I want people to walk through the doors and feel like they’ve stepped into somewhere they want to linger, not simply somewhere they came to shop.
And then there’s the creativity that comes with simply running a business. Every day requires problem-solving, whether it’s figuring out how to navigate a challenge, rethink a strategy, market a new idea or find a better way to connect with our customers. I’ve learned that creativity isn’t limited to designing a beautiful product. It’s a way of thinking.
That may be the part of my job I love most. I get to be creative every single day—in what we make, how we tell our story, how our stores feel and how we solve problems.
Are there any apps, books, podcasts, blogs or other resources you think our readers should check out?
My most-used app is probably the Notes app on my iPhone. I keep running lists of to-dos, ideas, reminders and random thoughts that I don’t want to lose. It’s simple, but it’s become my second brain. When I have an idea, I write it down—and I’m always surprised how often those little notes eventually turn into something bigger.
I also revisit Unreasonable Hospitality by Will Guidara every year. It’s one of the most influential books I’ve read when it comes to customer service and the idea of creating experiences people genuinely remember. It completely changed the way I think about our customers and how we can make them feel seen, welcomed and valued.
When I need creative inspiration, I turn to Pinterest. It’s one of my favorite places to pour gas on an idea—to see something from a different perspective, discover an unexpected reference point or push a project further than where I initially imagined it.
And for a dose of entrepreneurial reality, I love Guy Raz’s podcast How I Built This. Hearing other founders talk honestly about growth, failure, pivots and the realities of being a CEO is both inspiring and grounding. It’s a great reminder that behind almost every successful business is a long, winding story full of uncertainty, resilience and plenty of figuring it out along the way.
Contact Info:
- Website: https://www.fleastyle.com
- Instagram: @fleastyle
- Facebook: https://www.facebook.com/fleastylellc
- Youtube: https://www.youtube.com/@FleaStyle
