Today we’d like to introduce you to Kelsey Simon.
Hi Kelsey, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
Hi! My name is Kelsey, also known as @kelseysimonsays. I’m originally from South Florida, and I moved to Nashville four years ago after visiting on a road trip and realizing I didn’t want to leave. A month later, I bought my pink 1957 Thunderbird and named her Dolly Carton. That one impulsive decision completely rerouted my life.
What started as a fun side hobby turned into a full-blown creative business. I now rent out Dolly, along with her big sister Tonya Trucker, a 1959 F-100, for photoshoots, weddings, and events. I’m usually on-site helping with styling, posing, and behind-the-scenes content so guests leave with more than just great photos. They leave with a memory.
I partnered with White Velvet Chapel to offer Dolly Parton officiated “Best Babes” weddings, which are symbolic friendship ceremonies with custom vows, veils, a Dolly impersonator, and a pink getaway in Dolly Carton. We also do real weddings at the chapel, with Dolly or Tonya as the getaway car. Whether it’s romantic or ridiculous, I love helping create something unforgettable.
I also manage social media and events for Von Elrod’s, a German-style beer hall in Nashville, where I plan themed brunches like Dolly Brunch and Emo Brunch, film content, and build experiences that people actually want to be part of.
Along the way, I’ve teamed up with the iconic pink House of Adora and Katie-Mac Photography to bring bigger creative projects to life. Whether it’s styled shoots, pop-ups, or content campaigns, those collaborations have helped me grow the vision beyond just cars.
Nothing about my path has been traditional. I’ve followed what feels fun, meaningful, and creatively challenging and somehow it’s all come together.
We all face challenges, but looking back would you describe it as a relatively smooth road?
It hasn’t all been smooth. Not every idea was a hit right away. When we first launched the Best Babes Ceremony, we only had one booking. It took time to build momentum, trust my ideas, and learn how to market something that didn’t really exist yet. The slow starts taught me how to stay patient and keep pushing.
Alright, so let’s switch gears a bit and talk business. What should we know?
The Dolly Carton is a vintage car rental experience centered around a fully restored pastel pink 1957 Thunderbird named Dolly. She’s available for bachelorette parties, photoshoots, events, weddings, and music videos. I’m typically on-site to help with styling, posing, and capturing behind-the-scenes content so it feels more like a styled shoot than just a rental. It’s about creating something fun, memorable, and one of a kind.
Can you share something surprising about yourself?
What surprises people most is that I wasn’t a “car person” before this. I didn’t grow up in a garage or know the difference between models I just fell in love with one car and built a whole world around her.
Contact Info:
- Instagram: @kelseysimonsays
