Today we’d like to introduce you to Kimberly Jennings.
Hi Kimberly, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
I was born and raised in small-town Texas, and if there’s a common thread throughout my life, it’s probably community. Some of my favorite memories have always centered around gathering with family and friends and simply enjoying where you are and who you’re with. Those values have shaped everything from how my husband and I are raising our two daughters to the business I’ve built today. (Fun fact: I met my husband at Billy Bob’s Texas while he was performing in the house band, and years later we were married on that same honky-tonk stage.)
Professionally, I spent 16 years at Swoozie’s, a gift, party, and stationery retailer, where I started as a graphic designer and eventually worked my way up to Creative Director. It was an incredible place to learn, and I’m so grateful for the opportunities and experiences I had there. What I loved most was getting to see the entire life cycle of an idea—from concept and design to production, merchandising, marketing, and ultimately seeing it in a customer’s hands. Whether it was a birthday wine glass, a wedding invitation, or a funny cocktail napkin, there was something incredibly rewarding about being part of the process from start to finish and then watching people use and enjoy what we’d created.
Eventually, though, I hit a point where I knew I needed a change. I remember opening my laptop at the start of a new quarter and thinking, “I can’t do this again.” My creativity felt depleted, and for the first time in my career, I wasn’t excited about creating the next thing. Instead of pushing through, I decided to step back. I took some time to reset and figure out what was next.
During that time, my family took an RV trip to Wimberley. One evening, sitting on a hilltop overlooking the Texas Hill Country, I had a sense of clarity about my next step. That’s where the idea for Old Town Social Club really began to take shape.
Owning a business had never been a lifelong dream of mine—I simply felt called in this direction and followed it. As I started exploring ideas, I couldn’t ignore the growing popularity and cultural shift around trucker hats. What had once been a functional accessory was becoming a form of self-expression across demographics. People weren’t just buying a hat anymore; they were using them to tell a story about who they were, where they’d been, and what they loved. I saw an opportunity there and decided to take my first leap into entrepreneurship.
The inspiration for OTSC came from a place that was already meaningful to my family. We spend a lot of time in Old Town Burleson, where you’ll find live music, patios, local shops, farmers markets, festivals, and a strong sense of community. My husband plays shows there, our friends gather there, and we’ve made countless memories there. The feeling we get from that place—connection, laughter, hometown pride, and good company—is what became the foundation for the brand.
Today, Old Town Social Club creates hats, apparel, drinkware, and accessories centered around our motto: “Good Times with Good People.” We launched as a direct-to-consumer brand with a small collection of about 40 products sold through our website and local pop-up events. As the business grew, so did our catalog and customer base, eventually expanding into a wholesale and custom merchandise division, serving boutiques, businesses, event planners, and brands across the country.
Looking back, my years at Swoozie’s prepared me for this chapter in ways I didn’t fully appreciate at the time. Having worked across nearly every aspect of retail—from design and buying to merchandising and sales—I understand both the customer and retailer perspective. That experience has helped us build strong relationships and earn positive feedback for both our products and customer service.
The biggest lesson I’m still learning is to be content with the pace of growth. It’s easy to compare your journey to someone else’s, especially as a solopreneur, but I’ve learned that building a business while raising a family, being involved in my community, and taking care of myself means my story and path won’t look exactly like anyone else’s—and that’s okay. The older I get, the more I realize that success isn’t just about how fast you’re moving; it’s also about enjoying where you are while you’re getting there.
As we approach our second anniversary of OTSC, I’m incredibly grateful for how far we’ve come in just two years. What started as a season of rest and uncertainty has grown into something bigger than I ever imagined. I’m excited to keep serving our customers, growing the brand, and continuing to spread the “Good Times with Good People” spirit wherever this road leads.
Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
It definitely hasn’t been a smooth road, but I’m okay with that. There’s growth in every challenge.
In the beginning, the biggest hurdle was simply learning how to start and run a business. There was a steep learning curve when it came to things like business formation, taxes, licenses, trademarks, accounting, and all the behind-the-scenes responsibilities that come with being a business owner. Thankfully, my husband had been self-employed for years, so he was able to help guide me through a lot of those early questions and decisions.
Today, my biggest challenge is balancing growth with the rest of life. As a solopreneur, it’s easy to feel like you should always be doing more. There are always new products to launch, new social media ideas to test, and new opportunities to pursue. But I’m also a wife, a mom, a friend, a part-time Director of Marketing for a local private school, and a church youth leader. Learning to pursue growth without sacrificing those other priorities is something I’m still working on every day.
The good news is that I genuinely love what I do. Even on the hard days, I wake up excited to get to work, and that’s a gift I don’t take for granted.
Alright, so let’s switch gears a bit and talk business. What should we know about your work?
At its core, I help people and brands share their story and what brings them joy. Whether it’s a brand trying to connect with its audience or an individual connecting with a message on one of our OTSC designs, I love creating products that feel meaningful and authentic.
I keep a close eye on trends, but I’ve always had a bit of an old soul. My favorite designs are the ones that feel fresh and current while still having a timeless quality to them. In many ways, that’s what Old Town Social Club is all about—capturing the spirit of the good ol’ days in a way that feels modern.
I think what customers appreciate most is that I genuinely care about getting it right. I love collaborating, sharing ideas, and helping people find a direction that feels true to who they are. In return, they place their trust in us. Whether it’s a custom client coming back for their next project or someone stopping by our booth to tell us why a particular design resonates with them, there’s no greater compliment than knowing we’ve played a small role in helping celebrate their story.
What matters most to you? Why?
More than anything, I want to be a good person and raise good humans. I want my life to be marked by kindness, generosity, and love for others. Success comes and goes, but the way you treat people leaves a lasting impact. Whether it’s through my family, my business, my church, or my community, I hope to be a light, inspire others to do the same, and leave every place a little better than I found it.
Pricing:
- Retail hats: $28.95–$32.95
- Graphic tees: starting at $24.95
- Foam party cups (set of 10): $12.95
- Custom hats: starting at $19 each
Contact Info:
- Website: https://oldtownsocialclub.com
- Instagram: https://www.instagram.com/oldtownsocialclub.shop/
- Facebook: https://www.facebook.com/oldtownsocialclub.shop/
- Other: https://www.tiktok.com/@oldtownsocialclub.shop?is_from_webapp=1&sender_device=pc
Image Credits
@littlewesternfarms
@sierrasoapboxcandleco
