The Carriage and Happy Trails Outfitters are Tied by the Knot

SAN ANGELO, TX — “Year one, we had to figure it out,” said Jessica. Her mother and business partner at The Carriage Hip and Swanky, Vickie Housley, added, “We complement each other very well. Where I have weaknesses, she is strong and vis versa. We make a great team.”

Some may not know that the daughter of the mother-daughter team at The Carriage, located at 3029 Knickerbocker Rd, expanded her local retail empire through marriage. Jessica married Colby Cheshire who owns Happy Trails Outfitters.

Jessica said one of the biggest challenges of their marriage is to know when to turn the business conversation off.

Happy Trails Outfitters, located just up the road at 2023 Knickerbocker Rd in the Stadium Park Shopping Center, follows Colby’s passion for the outdoors. He he developed his passion as a youth leader in Young Life where he took many trips to Colorado hiking and camping. His store is the ultimate outfitter for outdoor activities, like hiking, running 5Ks, and jogging (and sandals in the summer months). He said among his favorite services he provides customers is helping them with shoes. Happy Trails carries brands like Brooks running shoes for runners, for example.

“What I like about helping people with shoes is that I am typically fixing a problem for them,” Colby said. Poor-fitting shoes can cause a myriad of health problems, back pain, or foot pain. Colby has the knowledge and the brands behind that knowledge to fix those issues.

Meanwhile, Jessica and mom carry trendy fashion lines for the ladies, like Birkenstock footwear. Also The Carriage sells the practical and fashionable Jon Hart luggage that’s handmade in Texas. Vickie’s favorite is the Happy Everything line, and extensional line of flatware, bowls, vases, and picture frames, sold in bases and attachments.

Jessica tributes their late father and Vickie’s husband, Kevin Housley, who died too early, just two years after he helped who he called “his girls” purchase The Carriage. This is particularly touching because Kevin’s father, and Jessica’s grandfather, Bob Housley, passed away this week. Bob Housley was a great man and business leader who helped not just his own family’s businesses, but also helped many San Angelo business owners thrive.

There’s much more to this story about Jessica and Colby. Watch the video above for many more surprises.