The list of current and former Philadelphia pro sports players, staff, and celebrities who have worn Jay Pross’ designs is long and includes names like Eagles players Cooper DeJean and Eric Allen, actor Bradley Cooper, and Eagles Head Coach Nick Sirianni.
“When he first became our coach, I sent him a handwritten letter with a bunch of shirts just saying, ‘Welcome to Philly, we got your back if you need anything,’” Pross, owner and creative director behind Art History 101, said. The two now exchange Christmas cards.
You can spot Pross’ designs easily enough around Philly. They’re usually bold, illustrative and retro-looking; the message is often tongue-in-cheek (like this “Lawnmower Man” design of offensive lineman Landon Dickerson who, after signing an $84 million contract extension, told a reporter he would buy a lawnmower) and it feels like you’re sharing an inside joke with the rest of the city.
“My roots in Philly just run so deep and I think people can see the authenticity,” Pross said. “The designs we put out, they are so relatable to people that love Philadelphia.”
Pross frequently collaborates with players on designs and invites them to the store in North Philadelphia’s Mayfair neighborhood for a meet-and-greet, like he did earlier this summer with Australian-born Eagles left tackle Jordan Mailata, whose “The Man From Down Under” shirt has become popular.
Pross loves to capture significant cultural events on T-shirts too: The moment Saquon Barkley pulled the insane move of a reverse hurdle over a Jacksonville Jaguars defender in a November 2024 game, Pross knew he had to put that on a shirt.
His newest Eagles-themed release features Eagles legend and chief security officer Domenico “Big Dom” DiSandro, reimagined as your favorite senior class president.
Sneak peek: For the upcoming season, Pross teased two new releases — a biker-themed Eagles design, and a design featuring the Frankford Yellow Jackets, Philadelphia’s first NFL team.
If you’re looking to stand out this season and own a piece of the cultural Zeitgeist, Art History 101 is the place to go.
