The signature splat shape of the old Bill’s Barbecue sign. The striking red “Lounge” neon lettering that lives above the bar at Helen’s Restaurant. The ingredients of a proper Hanover tomato sandwich. Westland Shopping Center’s iconic green cactus neon sign.
Local imagery like this factors heavily in the work of Harper Dobey, an artist who creates bespoke hand painted tote bags, pairs of pants and other outerwear. Sold under the name Silly Cowgirl, these items reflect Dobey’s obsession with Americana of the past century.
“Mostly, vintage American branding is my go-to,” says Dobey, a 25-year-old whose father Doug is a graphic designer known for his role in the city’s punk scene in the ’80s. More recently, he suffered a stroke which spurred a large local benefit concert in 2022; Harper has been helping with his recovery while running her business.
Having spent her entire life in the area, Dobey knew that locals would appreciate sporting some Richmond-specific flair. Growing up on Laburnum Avenue near a Bill’s Barbecue location led Dobey to include the sign of the now-defunct local chain in her art. The same nostalgia inspired references to Helen’s, a restaurant and bar that’s existed in the Fan since 1935.
“I went to Helen’s a lot growing up,” she says. “I worked there for a little bit. I’m still there twice a week.”
For the chef at Helen’s, who grew up in Hanover County, Dobey created the tomato sandwich pants, featuring Hanover tomatoes, a jar of Duke’s Mayonnaise, salt and pepper shakers, and a loaf of Martin’s Potato Bread. He loved them.
Dobey has an eye for little details. One of her Helen’s bag features a pomegranate and a pomegranate martini because there’s a seldom noticed picture of a girl holding a pomegranate on the restaurant’s wall.
Pennants are also a major element of Dobey’s work, reflecting her and her father’s love of the felt flags. With a collection that now numbers more than 50, Dobey favors weirder ones, like a pennant for an optical illusion house in Montana. “Everyone loves pennants,” she says. “They’re just such a good collectible.”
When Dobey takes a new commission, she tries to find a pennant of the city or state of where her client is from and add painted replicas to her client’s work. She’ll also look at her clients’ social media handles for other personal touches to include, like their favorite soda or the name of a pet.
Once, when Dobey was commissioned to create hand-painted pairs of pants for an entire bridal party, she included the initials of each of the women’s partners in the design.
Dobey says drawing her initial sketches on paper and figuring out the proportions and color scheme is the longest part of the process. Altogether, it generally takes about 12 hours of work to produce a new tote bag or pair of pants. While she accepts commissions sent to Silly Cowgirl’s Instagram handle, she prefers to get them via email or through her website’s submission form.
Currently, Dobey has some of her wares on display at Blue Bones Vintage. This Saturday, she will have a pop-up market at Pamplemousse Gallery from noon to 4 p.m.
Asked about the name Silly Cowgirl, Dobey says she’s long had an obsession with the American West.
Initially, her business was more focused on selling vintage clothing. She wanted to operate under the name Rodeo Clown Vintage but found that businesses already existed with that label. Desiring something that involved cowgirls and gave off a clown-like vibe, she went with Silly Cowgirl.
“It’s way more perfect than a rodeo clown,” she says. “That’s me: I’m a silly cowgirl.”
Silly Cowgirl has a pop-up show this Saturday, Jan. 27 from 12-4 p.m. at Pamplemousse Gallery, 300 N. Robinson St. For more information, visit sillycowgirl.com.
