WHO WE ARE
Welcome to Happy Jack Cap Co—where tradition meets customization.
Founded in 2024, we are passionate about reviving the classic blue-collar aesthetic of the 70s and 80s through our fully customizable caps. Our mission is simple: to provide you with a cap that not only represents your brand but also tells a story.
IT WAS ALWAYS ABOUT NOSTALGIA
When looking for blank hats for her clients, our founder, Connie Collingsworth, was hitting roadblock after roadblock. Either the cost was prohibitive, the fit was bad, or the materials were lacking. She knew what she wanted but couldn’t find it.
For Connie, it’s always about nostalgia. She wanted something that harkened back to the style of caps from the 1970s and 1980s. The solution was simple: if you can’t find what you want, build it yourself. In the process of researching and tweaking, she found her inspiration.
At Happy Jack Cap Co., we draw inspiration from Connie’s dad, the legendary “Happy Jack” Collingsworth, and his five brothers. These hardworking men embodied the spirit of resilience and craftsmanship, values that continue to guide us today.
We believe that every cap should be as unique as the person wearing it, which is why we offer an extensive range of options for you to create your perfect headwear. We can provide any type of cap you’re looking for, including our Classic Farm and Seed-inspired builds, Camp Caps, and Foam Truckers.
EASTERN KENTUCKY
With deep ties to Eastern Kentucky and the middle of Appalachia, Connie was surrounded by a family of strong, working-class men and women. Central to this group was her dad, Jack, and his five brothers. They were coal miners, mechanics, hunters, fishermen, military men, ham radio operators, gentle men, loving men... family men.
With her inspiration and research firmly in hand, she created a cap for her dad and each of his five brothers. These caps tell their stories. The colorways are vintage, the build is vintage, and the feel is expressly blue-collar.
Happy Jack began with a simple idea: bring back the kind of caps we grew up around. But something happened.
What started as a way to honor Happy Jack and the Collingsworth brothers quickly grew into something more. As friends, touring bands, small businesses, and brands began asking for custom caps, we saw an opportunity to do things differently. Rather than decorating generic blanks, we set out to design our own flagship cap builds, giving our customers better-fitting caps, better materials, and the freedom to create something that truly felt their own.
Folks today scour flea markets and online vintage shops searching for that nostalgic look and throwback fit. If you find a wearable cap in those places, they come at a high-dollar markup. We can provide that very style with high crowns and deep fits at a reasonable price, while also allowing you to create custom runs for your business, brand, or band.
Today, every Happy Jack cap is rooted in the same values that inspired the first one: honest craftsmanship, timeless design, and the belief that the things you use every day should only get better with age.
FOUNDER & CREATIVE DIRECTOR
Connie Collingsworth
“This is America. Pick a job and become the person that does it.” — Mad Men
Connie got an early appreciation for design and ephemera when Happy Jack and her mom would take her to flea markets and junk stores as a kid. It also wasn’t unusual for them to hop in the car and make the drive down to Nashville on weekends for Jack to peruse the used record stores and pawn shops. Connie took it all in, and that’s where the roots of her design journey began.
Connie started her creative career in 1997 when she co-founded Print Mafia with her longtime friend and fellow artist, Jim Madison. Together, they created concert posters and art prints for 20 years, working with venues and bands from around the country.
Her career pivot to art direction and music merchandising started in 2016 when she began working with her first touring client, Colter Wall. Since then, she has worked with other artists and brands, including Waylon Jennings, Wynonna Judd, Sturgill Simpson, Turnpike Troubadours, Marathon Live!, Turkey and the Wolf, Smith + Rogue, PopStroke, Chicago Music Exchange, and more.
Connie took the next logical step in 2019 when she co-founded La Honda Records with friend and industry colleague Travis Blankenship. La Honda is a passion project that has allowed her to put out music she believes in by artists she respects.
Now, with Happy Jack Cap Co., her career has come full circle to Creative Director and Product Curation.
Connie is a proud member of the Honorable Order of Kentucky Colonels. When she isn’t working, Connie can be found watching her favorite movies, TV programs, and football, collecting ephemera of all sorts, hanging out with her two dogs and cat, adventuring with her wife and business co-owner, Stacey, and being an all-around un-cool person.
SIX BROTHERS
Happy Jack was one of six Collingsworth brothers, and each of them left their mark on our family in different ways. They were veterans, mechanics, miners, hunters, tinkerers, storytellers, and family men. Each had a personality all his own, but they shared a deep appreciation for hard work, good company, and a life well lived.
Bill Collingsworth
I was always drawn to and fascinated by Uncle Bill. He had served in the Vietnam War, and from my earliest memories, that confused me because he always looked and sounded like the peace-loving hippies I’d seen on TV. He has always been a thoughtful man. I admired that, along with his intelligence. When Bill would regale us with stories from his travels, they always focused more on the people than the places. Bill was, and is, adventurous and up for anything. I wish more of that had rubbed off on me. I do know that Bill was always interested in what I was doing. He was constantly encouraging me, and really everyone to live a full life. My Uncle Bill is the last of the brothers still with us and I’m glad for it.
The "Bill" cap is Fatigue Green paying homage to his vast military service. There is also a Vietnam style helmet pin.
Charles Collingsworth
My grandparents had this photos of Charles framed and proudly displayed in their living room for my entire childhood. I was fascinated with it. He looked like a movie star from some old black and white war film to me. Of all the brothers Charles was the only quiet one. He was more reserved and definitely seemed like the caretaker of the brothers. Whether they saw it that way I’ll never know. He always seemed like a hard working, decent kind of guy just doing his best to get through the world. The signature “Charles” cap is tri-colored dark blue, sky blue and cream with dark blue metal eyelets. It is based on the Air Force colors of his military service to tie it back to this amazing photo.
Don Collingsworth
Don was a big guy. Bigger than the other brothers in stature. Bigger in personality in some ways. All the brothers were funny, great storytellers, and family men, but something about Don always felt “solid” to me. Growing up, I knew we were gonna hear some tales from Don. I know now that they were all embellished for effect, but from him they felt like they may have happened just the way he told them. Try to imagine an Eastern Kentucky good ole boy version of John Goodman. That was Don. Don met his future wife Brigitte while stationed in Germany. He married her, brought her home, and they had two kids. Marrying someone from a totally different way of life seemed so exotic to me. I can’t tell you the joy that culture clash brought to our family. Don was an avid hunter and fisherman. Most of the brothers were, but he was the “Sportsman”. Don fought cancer valiantly and I think his spirit carried him far, but he did finally succumb to the illness. I know his family misses him terribly, as do all who knew him.
The "Don" cap is Deere Green with Hunter's Camo underbrim, contrasting off-white stitching, and metal eyelets.
You will also find pins that were inspired by Don’s love of the outdoors: a Deer head, a jumping fish and tackle box.
JOe Collingsworth
Uncle Joe and his wife Joleen lived closest to us when I was growing up. It wasn’t uncommon for us to make the short drive to their house often for quick visits. My Dad and Joe always seemed to have some little project they were working on in the garage – fixing a motor, tearing an engine apart, evaluating some old truck Joe had “gotten a deal” on. My Mom cooked a big family meal every Sunday and, more often than not, Joe was at those dinners. He had a big appetite. Not just for food but for fun and mischievous behavior. Those meals always turned into evening poker games with everyone drinking way too many cups of coffee (Joe always had a cup of coffee in his hand) and us kids hanging on the backs of chairs wanting Joe’s attention. He was a big kid with an even bigger heart, which was ironic because he was born with a heart condition. He was a “blue baby” and the brothers would chase him around the yard when they were kids to see him turn blue and pass out. There was always something happening with Joe and his heart doctors. I remember often hearing the convos about his health between the adults. I also remember when his heart finally gave out at a young age. His absence left a huge hole in our family and it was especially hard for my Dad.
Wayne Collingsworth
Wayne was a fixture down at the Middlesboro KY American Legion. He loved his beer, cigarettes and country and Bluegrass music. I dare say no one ever looked cooler in a trucker cap. All my uncles and my Dad were members of “the Legion”. I spent a good deal of my youth at these type of establishments with my parents. There’s something about a tavern (not a bar) that’s was amazingly comforting as a kid. I’d sit at the bar and the bartenders would make me cherry cokes and cheeseburgers while Mom played Bingo and Dad played cards and was fleecing people out of cash and pink slips in the back room. The jukebox was never silent with a constant stream of classic country. The neon beer signs made a glow that I still love to this day. The women were the best kind of “broads” and the men were all charming jokers. Wayne was definitley a charming joker. Wayne had a red mustang for a while and I thought it was the coolest. The “Wayne” cap, which is a rich, smooth Mustang Red color was inspired by his car and also a vintage beer bottle pin to remind me of the Legion.