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‘That’s drip right there’: This Mayfair artist wants to put Philly on the U.S. streetwear map

Jay Pross’ designs aim to celebrate North Philadelphia, an area he feels is not widely represented.

Jay Pross, owner of streetwear company Art History 101, addresses a crowd on the 7000 block of Frankford Avenue during the Mayfair 2nd Annual Arts Festival on April 13, 2019.
Jay Pross, owner of streetwear company Art History 101, addresses a crowd on the 7000 block of Frankford Avenue during the Mayfair 2nd Annual Arts Festival on April 13, 2019.Read moreEDWARD NEWTON

This story is part of Made in Philly, a series about young residents shaping local communities.

The shirts decorating the walls of Art History 101 reflect Jay Pross’ childhood in Northeast Philadelphia.

One of his favorites shows a man cranking open a fire hydrant and kids running through the spraying water.

“That was our beach growing up,” Pross, 35, the artist and entrepreneur who owns the streetwear shop, said about the design.

Pross’ mom, a single mother with three other kids, would try to make an annual family trip to the Shore for a day because they couldn’t afford to stay the whole weekend. That meant Pross, whose full first name is Justin, spent his summers cooling off in the streets of Philadelphia.

His brick and mortar store, Art History 101, recently hit its nine-year mark since doors opened at 7045 Frankford Ave. The business has grown from about $90,000 in sales his first year to more than $300,000 last year.

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For Pross, his business represents more than his love of street art. His streetwear designs aim to celebrate Northeast Philadelphia, an area he feels is not widely represented. It has been a path to the middle class for his family. And he hopes his success can be an example to other kids who love art that they, too, can become entrepreneurs.

Pross recently bought a truck for $17,000 that serves as a mobile boutique, equipped with hardwood floors, shelves, racks, and a dressing room. He plans to take his shop on the road, whether that is to other parts of Philadelphia during a lunch hour or to other cities across the country. Logos and monograms are staples of streetwear branding, like the star next to the letter H that Pross uses to distinguish Art History 101.

Streetwear is influenced by both music and culture and at any time, could be considered surfwear, skatewear, hip-hop, punk, East Coast- and West Coast-driven, or even high fashion, said Elena Romero, who wrote the 2012 book Free Stylin’: How Hip Hop Changed the Fashion Industry. The style became a global phenomenon in the mid 1990s, but urban, hip-hop streetwear is making a resurgence along with ’90s fashions, which can be seen in popular brands like Supreme and FUBU or on the shelves of Urban Outfitters and H&M.

“It’s just basically, to me, clothing that young people wear, and that derives from different cultural movements,” said Romero, who is also an adjunct assistant professor at the Fashion Institute of Technology in New York City. “You’ve got a new generation that is either creating their own brands and putting their own spin to it, or rediscovering preexisting brands, or bringing brands back to life, wanting to connect to hip-hop history.”

The U.S. urban streetwear market was estimated at $80 billion in the U.S. and $175 billion globally in 2015, according to Statista, a market and consumer data provider, and the market saw growth in 2017, according to a Bain & Company report.

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Pross wants to see people as far away as California and as close as New York City wearing his clothes, the same way people from Philadelphia wear clothing bearing the names of other cities.

“I will continue to represent my city until we get there,” he said.

‘This is my dream’

His mother, Barbara Pross, remembers when the utilities in their home shut off and Pross would ask, “Do we not have hot water or did you forget to pay the gas bill?” The kids didn’t know any different and Barbara Pross tried to shield them as much as she could from the family’s shaky finances.

A couple of times she said she missed utility payments because she wanted to use the money for gifts so the kids would have a nice Christmas. Other years, they were able to participate in Toys for Tots, and once a friend bought them a Christmas tree.

Barbara Pross, 63, encouraged her son to pursue his love of art, though she wasn’t a fan of the graffiti fines he would rack up. Every Christmas she would hand him a black book and say, “This is what you’re supposed to draw in.”

When he was 18, Pross used paint stencils to make a shirt for a friend’s funeral. People started asking for them. He made 20 shirts, sold at $10 a piece, and quickly realized he could make a career out of his talent.

He attended the Art institute of Philadelphia for fashion design and worked at Philadelphia-based urban luxury clothing brand Miskeen Originals when the company designed a hoodie for the Soulja Boy “Crank That” music video and the Pink Panther T-shirt Bun B wears in Beyonce’s “Check On It” music video. After celebrities started wearing Miskeen designs, friends encouraged him to start his own business.

His mother and sister, Heather, 40, volunteered to work at his store for free. Now, almost a decade later, they are employed full time and get steady paychecks.

Pross estimates about 65 percent of purchases are made in store and 35 percent are online.

“I can relax and go to sleep at night knowing that my bills are paid,” Barbara Pross said. “Now I’m just worried about retirement.”

Pross’ talent for graffiti-style art can be seen in designs throughout the store. A $26 black T-shirt displaying the text “The Philadelphia Dream” hangs on the wall. The lime green bubble letter text on top of a bright pink outline was inspired by the TV show Fresh Prince of Bel Air starring West Philadelphia "born and raised” Will Smith. Limited edition shirts come with a certificate of authenticity.

And there are many Philadelphia sports-themed shirts, like a newly released Ben Simmons design.

When Pross started his business, he and his mother were renting their homes. Now, they own them.

“I look at them like they’re my trophies,” he said.

'My golden ticket’

Pross knew Eagles wide receiver Nelson Agholor was doing a meet and greet at the Exton Square Mall in November 2017 so he took a print of a Brian Dawkins “Bleed Green” design and asked him to sign it.

“I’ll give you my number. Maybe we could do a collab on something," Pross said, according to a video from the interaction. "I’ll put you like this ...”

“I bet,” Agholor said, looking up after writing “Go Birds!” on the print. “I want the fallback. I want the fallback on a hoodie.”

Two months later, Pross went to another meet and greet at the Oxford Valley Mall to follow through.

“Remember the last time we met, what you asked me for on a shirt?”

“Yeah, let me see,” Agholor said. Pross placed the design in front of Agholor.

“That’s drip right there, that’s, that’s wet," Agholor said. “I need that in a hoodie.”

“Let’s put it out,” Pross replied.

Agholor agreed and they shook on it. The shirt debuted Jan. 19, 2018, two days before the Eagles played the Minnesota Vikings in the NFC Championship game. The $26 shirt and $50 hoodie still sell at Art History 101, and the website includes a photograph of Agholor’s signature of approval on the design.

The shirt has been one of the store’s top sellers and Pross said he couldn’t make them fast enough when it first came out.

“I just go where they go with my shirts,” Pross said of his marketing strategy. “I always say they’re my golden ticket.”

When he isn’t working, Pross is figuring out ways to give back to the community.

He helped plan the Mayfair Arts Festival, the second this year, participated in others like the 2nd Street Festival, helped start a fashion show in Mayfair last year, and has spoken at schools to encourage students to follow their passions and had students shadow him while working.

Marc Collazzo, executive director of the Mayfair Business Improvement District, called Pross’ shop “unique” and “dynamic" and said it was an example to other businesses that if someone has a great, new idea, it can work in Mayfair.

“There’s no one like what he does. It’s not a T-shirt shop. He’s an artist where you can get his brand. So it becomes a destination," he said. “It shows that you can start something and be creative and be very successful.”

Outside Pross’ bustling store on a recent Saturday were racks and piles of shirts on sale. While most shirts are usually $25 to $28, the store always has a couple of tables of shirts for $15 and some on clearance for $5.

A handful of times a year they release an exclusive $10 shirt, because, Pross said, he wants to make sure anyone can afford his art.