Aaron LaCrate made his first T-shirt using a black Sharpie to trace a band logo on a shirt stretched over an album cover. He was 8 years old. That was many years and many T-shirts ago, long before he moved to Manhattan and started his own clothing line, Milkcrate. Nowadays, his shirts and hoodies sell at Urban Outfitters and online for upwards of $80. Back in 1983, the kids in LaCrate’s Highlandtown neighborhood didn’t have a local shop—or, probably, the money—to buy punk-rock shirts. So they made their own, starting with a Suicidal Tendencies record. “We traced the design directly onto the shirt,” says LaCrate. “Some of them were great and looked just like the album. And some of them were so bad they were good.”

Sitting in a Fells Point coffeeshop during a recent visit home, he smiles at the memory. At 38, LaCrate still has a boyish face and the youthful enthusiasm to match, especially when it comes to his local roots. Throughout the mid-to-late 1980s, he and his friends were listening to punk rock and hip-hop, writing graffiti, and skateboarding. They hung out in basements and underground clubs, where LaCrate spun records as DJ Cool Aaron.

“I grew up in the most glorious era of Baltimore street culture,” he says, before ticking off a list of local “legends” that favors graffiti artists like Adam Stab and club-music figures such as DJ Equalizer. “I was a sponge for all these different aspects of urban culture. I soaked them up.”

LaCrate applied that street cred to Milkcrate, now in its twentieth year. His T-shirts, hoodies, and hats have been especially popular with rappers, and everyone from Eminem to Schoolboy Q, who recently rocketed to the top of Billboard’s album chart, has donned Milkcrate gear over the years.

And when Complex, the New York-based fashion magazine, recently chose its “50 Greatest Streetwear T-Shirts of All Time,” two Milkcrate designs made the list alongside iconic images like Shepard Fairey’s “Obey” and the Wu-Tang Clan logo. “Can you believe I’m in that kind of company?” asks LaCrate.

LaCrate also designed HBO-licensed shirts for The Wire, collaborated on limited-edition products for New Balance and Beats by Dre, and created a line of shirts with John Waters, who praises him for being so ambitious, but never selling out.

Milkcrate’s 2014 summer line—heavy on bold colors and tie-dye—debuts this month. The hot items figure to be Milkcrate’s bucket hats, similar to the LaCrate-designed hat that Schoolboy Q wears in his “Man of the Year” video, which has 15 million YouTube views.

It’s been an impressive run, with a few equally impressive detours that have taken LaCrate, the DJ, around the world and to festivals like Bonnaroo.

When asked about the secret behind his staying power, LaCrate shrugs off the question. “I’m just a kid from Highlandtown,” he says. “I never stop hustling.”

But it’s more complicated than that.

When LaCrate was a youngster, a typical Saturday involved taking the number 10 bus downtown for art supplies and records. He bought markers, sketchpads, and spray paint at Nyborg’s or Adcom. Though his graffiti-artist friends were notorious shoplifters, he saved his money, he says, and paid in full. Then, he hit the record stores along Howard Street, digging through crates of vinyl at Crazy Gump’s (which became Inner City Records), Music Liberated, and Dimensions in Music, searching for obscure gems. On some occasions, he might have shopped for clothes at The Gallery, before heading back to Highlandtown.

He bused tables at Obrycki’s—saving tips to buy turntables on layaway at Inner City—and bonded with the guys in the kitchen from the nearby Flag House projects. He hung out with older kids, who got together to draw, listen to music, and drink, snort, or smoke whatever substances were available. Some of them stole cars for fun. “It was a wild, outlaw kind of world,” he recalls, “and everyone was hustling to make money, do graffiti, or make their mark in some way.”

LaCrate shied away from the criminal activity. “Kids all around me might be smoking PCP, but I’d just sit there and draw or DJ,” he says. “That’s because I was raised to be scared of drugs. I was raised to be scared of everything in my neighborhood.”

Here’s where LaCrate’s story diverges from many of his peers. Unlike most of them, he enjoyed a stable home life, with married parents. His father cut hair at a Parkville salon; his mother was a stay-at-home mom, who didn’t tolerate foolishness from Aaron or his older brother. They stressed getting a good education and sent Aaron to Boys’ Latin, Cathedral, and Loyola Blakefield. They signed him up for soccer, lacrosse, and even skating at the Dominic “Mimi” DiPietro ice rink.

“My parents were cool, but very strict,” says LaCrate. “They kept tabs on me and made sure there was no extra room to be doing drugs and things like that.”

They nurtured his artistic talents, buying him sketchbooks and spray paint for Christmas, and when his athletic interests shifted from team sports to skateboarding, they got behind that, too. “At that time, it was still a fringe thing,” says LaCrate. “If you were into skateboarding, you were considered a freak, a weirdo. The only skateshop I knew about was all the way in Towson.”

His father, sensing a business opportunity, found a distributor in Ocean City, bought a dozen decks and a dozen T-shirts, and started selling skateboards out of the basement of the family’s row home.

It wasn’t long before his son started making T-shirts and mixtapes of hip-hop and club music in the same basement.

By the time college rolled around, LaCrate had his own cottage industry going. But at Syracuse University, he says, “Everything I’d done in Baltimore didn’t count for shit.”

He majored in communications and began anew, hosting two hip-hop shows on the college radio station, booking campus concerts for the likes of De La Soul and Nas, and becoming a college rep for a few record labels.

He continued making shirts and mixtapes, which he sold for $5 at the college bookstore and publicized by plastering fliers on every bus stop in the area. “That sort of promotional thing was second nature to me by then,” he says, “and I was completely insane about it. I had to make things happen.”

After graduating, he moved to New York and went to work for booking agent Jerry Ade at Famous Artists Agency in 1997. “It’s the only real job I’ve ever had,” says LaCrate, before correcting himself. “That, and Obrycki’s. But it was a whole other playground.”

“Aaron worked hard and learned quickly,” recalls Ade. “He did an excellent job for us.”

LaCrate booked shows for, among others, Eminem and Jay-Z, sometimes brokering deals with shady characters. “It was a whole new set of criminals,” recalls LaCrate. “It was a lot like what I’d experienced in Highlandtown, but on steroids. Growing up in Baltimore had prepared me for it.”

On the side, LaCrate continued designing shirts, which he sold under the Milkcrate label—its name and logo a nod to days spent digging through milk crates full of records. He passed along Milkcrate clothes to the artists he booked. “They liked them,” says LaCrate, “because I was such a music kid, and the shirts reflected that. Instead of DJ’ing, I was making DJ-inspired streetwear.”

With the likes of Eminem wearing his shirts, Milkcrate was “going full blown.” So he quit his day job.

As Milkcrate spread internationally to cities like London and Tokyo in the early-to-mid 2000s, LaCrate was asked to represent the brand at openings and parties. His hosts hoped he might do something besides stand around and make small talk, and that’s what got him back into DJ’ing.

He’d spun mostly hip-hop in college, but felt the genre was too oversaturated for his brand, which he considered more counterculture. So he returned to his underground roots and club music, which hadn’t broken beyond the city limits, and found it played well with audiences who’d never heard it. In 2005, he produced a club-inspired CD, Bmore Gutter Music (featuring Spank Rock and others) and got national distribution for it.

Around the same time, the scene started drawing outside attention. International recording artist M.I.A. and DJ/producer Diplo embraced Baltimore club and collaborated with local hero Blaqstarr, club king Rod Lee scored a positive review in Pitchfork, and a rumor circulated that Pharrell was taking interest.

As the music’s commercial potential increased, various figures laid claim to it and sparred for attention. “I considered Gutter Music to be a next level thing,” says LaCrate. “I just replanted the flag and helped put the spotlight on Baltimore. ”

He parlayed the notice into DJ gigs with British stars Lily Allen and Dizzee Rascal. He performed at Bonnaroo and the Pitchfork Music Festival and shared bills with celebrity DJ Mark Ronson.

Since the club music buzz waned, LaCrate has continued DJ’ing and notes that the clothing is currently “on an upswing,” though it’s still a mom-and-pop operation. LaCrate designs all the clothes himself, while his girlfriend deals with the production, or “cut-and-sew” side. “It’s as DIY as you can get,” says LaCrate. “There’s no backer or big investor.”

Going forward, LaCrate sees himself doing similar work for others. He plans to launch LaCreate—an advertising agency dealing with print, graphics, radio, digital, social media, and branding—and says he’s open to working with Baltimore clients. “A lot of brands don’t have much content behind them,” he says, “and I can help with that, because I have a recipe that works.”

When asked what the recipe is, LaCrate smiles and shakes his head: “I can’t say—it’s a secret, like the Colonel’s.”

He sounds intrigued by the prospect of contributing to other people’s projects. “I really don’t care about being famous,” he says. “I don’t care who knows about what I do. I care about shaping culture, because whoever shapes culture the most wins.

“That’s a lot for a kid from Highlandtown.”