PORTLAND, Maine — Leo Robinson, 14, held the screen printing frame steady as his father, Lewis Robinson, dragged a color-splattered squeegee down the front of a dark gray T-shirt in their Deering neighborhood basement on Thursday afternoon. Lewis Robinson then lifted the frame, set it on a nearby treadmill and revealed an image of the city’s former B&M Baked Beans factory emblazoned in white ink.
The graphic was complete with the iconic building’s now torn-down brick chimney and its famous, skeletal Christmas tree, always visible from Interstate 295 during the holiday season.
Leo Robinson then carefully folded the T-shirt and set it aside on the family ping pong table to dry with about a dozen others.
The pair were working hard to keep up with growing consumer demand for their nostalgic pullovers which also preserve Portland’s history, one T-shirt at a time. Each of their roughly dozen shirt designs, like the bean factory, pays tribute to a specific piece of the rapidly changing city’s long-gone past or beloved-but-endangered present.
Other designs the pair have printed in their basement workshop include the former Million Dollar Bridge (built in 1916 and closed in 1998), the old Greyhound Bus sign on Congress Street (which stood for 40-something years) and the fishing shacks at South Portland’s Willard Beach (which washed away in a storm earlier this year).
“People really connect with these shirts in an emotional way,” said Jessica Thompson, who owns Handiwork Studio+Market on Stevens Avenue, which sells the Robinsons’ shirts. “They’re probably our biggest sellers. Without the shirts, there’d be no Handiwork.”
Lewis Robinson, who draws all the designs, is not a professional artist. The almost life-long Portland resident is a novelist and associate professor of creative writing at the University of Maine at Farmington. T-shirts are just a side hustle.
He said he never had any kind of grand plan to preserve pictures of “Old Portland.” It’s just worked out that way.
For years, he just made small T-shirt batches for birthday parties, sports teams he coached and a summer writing camp he once ran. But about five years ago, a neighbor suggested he design a shirt around the Quality Shop, their beloved convenience store in Deering Center.
It was an instant hit with locals.
“It kind of took off from there,” Lewis Robinson said. “That place is so important, being across the street from several schools. All the kids started wearing it. That kind of fueled it.”
From there, he began thinking about other iconic bits of the city that would make for a good shirt. Being in his 50s, naturally, many of the places which came to mind were either gone or not quite what they used to be.
One of Lewis Robinson’s next designs depicted the Eastland Hotel’s big, red rooftop sign, complete with the stanchions which hold it up.
“My prom was held in there,” he said. “I see that sign and it immediately reminds me of being a teenager, making memories and getting in trouble in Portland.”
Since he began selling his shirts in 2017, Lewis Robinson reckons he’s sold thousands to both long-term Portlanders and newcomers alike. It’s just a guess, but he suspects newly local folks want to wear something that gives them a little street cred.
“And that’s OK,” Lewis Robinson said. “I do that when I travel to a new place, too. It makes you feel like you’re connecting with the insider vibe.”
Though too young to remember the Million Dollar Bridge, Leo Robinson definitely remembers JET Video (the city’s last video rental store which closed in 2018) and wears that design unironically.
“Kids like remembering their city, too,” he said. “I have great memories of going there for ice cream and to rent a video after school.”
After talking for a bit, the Robinsons had to get back to work in their subterranean art lair.
They had orders to fill.
