Winslett’s Way

Winslett Long Watson built a life and a career around turning the unexpected into something beautiful.

Words by Jenny Lynn Davis | Image by Christine Hall

A watercolor drip once changed the course of Winslett Long Watson’s life.

As a child, she joined her aunt, Phyllis Long, on an afternoon trip to the pond behind Memorial Park Elementary School. When a stray drop splashed onto her painting, Winslett felt her heart sink. Phyllis, an experienced artist, smiled and said, “Turn it into something else.” So, she transformed the mistake into a snow skier at the base of a tree.

“It wasn’t the pond anymore, but I loved it just as much,” Winslett recalls.

That early lesson in how something unintended can become something beautiful has guided her ever since.

Growing up in Jasper, she was constantly making something. “We didn’t have many kids in our neighborhood, so we made our own fun,” she says. “I even made a little newspaper and used my dad’s Xerox to copy and deliver it through the neighborhood.” Art was never a separate activity; it was simply how she experienced the world. Her parents encouraged her curiosity, and her aunt helped her see creativity as a form of play rather than a pursuit of perfection.

By high school, that imagination began taking shape in practical ways: painting run-throughs for football games, designing cheer signs, and hand-lettering T-shirts. She hadn’t planned to pursue art professionally, but a friend’s suggestion to take an introductory design class at the University of Alabama changed everything.

At Alabama, Winslett found the perfect balance of creativity and structure. She studied painting, printmaking, and photography while concentrating in graphic design, long before digital tools became the norm. “We did almost everything by hand,” she says. “I graduated right as Photoshop was entering the field.” Eager to master the new technology transforming the industry, she pursued her master’s at the Savannah College of Art and Design (SCAD), where she also fell in love with the coastal Georgia city that would eventually become home.

Savannah felt familiar. It was warm and welcoming like Jasper but brimming with creative energy. After earning her degree, Winslett joined the SCAD faculty, where she taught graphic design for five years. “I learn best in a classroom,” she says, “and teaching deepened my understanding of the art.”

When motherhood arrived, Winslett’s focus shifted again. After her first son was born, she stepped away from full-time teaching to stay home. “Our boys are just fourteen months apart,” she says. “When they started Mother’s Day Out, I launched a little business called Backyard Baby, offering personalized children’s clothing up to size 12.”

The business began as Winslett’s creative outlet, but quickly blossomed. As customers started requesting personalized linens and home goods, and as her own boys outgrew the styles central to southern boyhood, Backyard Baby evolved into Lettees, a name combining “Winslett” and “tees.”

Reinvention runs through all her work. When faced with excess or imperfection, Winslett doesn’t discard; she reimagines. Once, with a surplus of sample T-shirts printed with customers’ names, she cut them apart, dyed them, and transformed them into jewelry. That upcycled collection became one of her favorite projects and added a new dimension to Lettees.The same philosophy inspired her to paint on cardboard. “When we built our home, we had all these huge appliance boxes—beautiful, flat pieces of cardboard,” she says. “I started painting on them for myself, then framed a few for a fundraiser show, and they all sold. Turning something meant for the landfill into art feels good.”

Today, Winslett’s work includes murals, window displays, and fine art commissions that brighten spaces across the Lowcountry. Her two Savannah studios, one in a sunlit attic and the other in a riverfront cottage, provide both solitude and inspiration. “The Spanish moss, the marsh, the birds—it’s endlessly beautiful,” she says. “I can look up from the easel and feel peaceful and creative at the same time.”

Her work has been featured in Southern Living, HGTV Magazine, and Serena & Lily. Still, her greatest pride lies in the connections her art creates.

Looking back, Winslett can trace everything to that watercolor drip years ago. “Watch what you choose to do when no one’s telling you what to do,” she says. “That’s often what your soul is meant to do.”

It’s advice she’s lived by - following her instincts, embracing change, and finding beauty in imperfection. “I never set out to be an artist,” she says. “I just kept making things.”

And in doing so, she’s built a life that reflects her earliest lesson: when you approach the world with imagination, even the unexpected can become a work of art. 78