In 1995, Tupac and then-girlfriend Kidada Jones walked the runway for Gianni Versace’s Fall/Winter 1996-1997 fashion show. Draped in a gold velvet suit from the collection, he preceded to launch into an impassioned rendition of “California Love,” which made the Milan attendees turn from reserved fashionistas into G-Funk devotees.

It was a long and winding road from 2Pac’s time rocking Timberlands and Carhartt denim in Baltimore to being front and center as Versace’s personal guest and model. On paper, it may have seemed like a dramatic juxtaposition between Hip-Hop culture and haute couture, but Tupac’s fashion track record suggested a willingness to use his fame to uplift the Black community.

Tupac and Versace will forever be linked with violence, tragedy, and, in different ways, forward thinking. The late rapper possessed a keen understanding of his position to elevate others, in this case, designers on the precipice of greatness.

When the ’80s turned into the ’90s, the fashion industry began to see a shift from regional mom- and-pop shops to big-box department stores. As popular regional apparel became more accessible globally, it was no accident that it coincided with the explosion of Hip-Hop music. As today, music drove the fashion silhouettes of the era.

Elena Romero, assistant professor at the Fashion Institute of Technology in New York and author of Free Stylin’: How Hip-Hop Changed the Fashion Industry, vividly recalls this time.

To Brooklyn-born Romero, shows like Lifestyles of the Rich and Famous and brands like Polo and Nautica spoke of a narrative in which there were the haves and the have-nots. For kids worried about where they were getting their next meal, the idea of wearing designer clothing seemed a distant dream. In the tradition of Hip-hop, however, kids began to create their own outfits from what already existed, and a few savvy entrepreneurs took notice.

“The turn of a tide was when these Black entrepreneurs decided we need our own brands,” Romero says. “And for artists like Pac, just as he’s coming up and he’s watching things, it made perfect sense from a personal and a professional level. He moved in so many spaces. He was music, he was film, he was activism. If you’re drawn to his words, you’re going to be drawn to his style. I think it’s fair to say that if you have the attention of the masses, that your style will be imitated and replicated. I think it’s just the natural progression.”

Brands like Carl Jones and TJ Walker’s Cross Colours, Carl Williams’ Karl Kani, and April Walker’s Walker Wear signaled a new era of designs built around inclusion for minorities. According to Williams, fashion industry trade shows like MAGIC didn’t have people of color when he was launching his brand.

As a result, their brands were at the forefront of taking existing styles, reinventing them, and remixing them to embrace the aesthetic of the neighborhood shops of the ’80s. The streets were no longer just watching, they were participating.

“This was the first time that from a Black youth perspective or young people of color that we were able to show the power of our dollar,” Romero says.

These designers built their brands from the ground up by prioritizing their own experiences in their clothing. But they needed high-profile supporters who were cognizant of their role in society. 2Pac fit the bill.

“Back then, there was nothing like it on the market, and today it’s the nostalgia factor,” Williams said in Billboard. “Back then the only brands people were rocking were Tommy Hilfiger, Calvin Klein, Giorgio Armani, Ralph Lauren, Jordache, DKNY, and a few more. That was our competition, and I had to convince people that they didn’t have to rock them. I’d say, ‘Here’s what’s real. I’m going to give you the right fit, I’m going to give you the colors that we want, I’m going to give you the whole ensemble, the tops and the bottoms are going to match.’ ”

Tupac and Williams first met at Hotel Nikko on La Cienega Boulevard in Beverly Hills. When Williams ventured into Tupac’s smoke-filled room, he was typing a movie script. He never took his eyes off the screen as they talked about culture, film, and other facets of life. Williams eventually asked how much it would cost for him to do an ad for his brand. Tupac stopped typing.

“Yo, man,” Tupac ssid. “I’m not going to charge you, you’re Black. I don’t charge my people for nothin’.”

Tupac's only stipulation was that the “Thug Life” slogan, popularized by the arching tattoo across his midsection, would appear in some of the branding. Williams agreed. But before he could leave the room, Tupac already had an idea: He wanted to be photographed sitting on top of a basketball hoop. Two weeks later, that image was captured.

Tupac used every instance to tout the brand, notably at an interview at a Compton gun range, in the music video “Keep Ya Head Up,” and his first piece of press with Vibe after he was shot in New York City.

“I didn’t know I was shot in the head yet,” 2Pac told Kevin Powell. “I didn’t feel nothing. I opened my pants, and I could see the gunpowder and the hole in my Karl Kani drawers.”

The owners of Cross Colours and Karl Kani had uphill battles when it came to excelling in the marketplace. However, they were aided by a three-year partnership and a key account with popular big-box store of the era Merry-Go-Round, which was worth upwards of $100 million. Walker faced additional challenges as a woman in a male-dominated field. But she wasn’t deterred from entering the fray.

“You had to know how to play chess,” Walker says.

“You had to sometimes stand on the table and stomp, and sometimes you had to know when to fall back. And sometimes you had to know how to make a man make himself feel like he is creating an epiphany moment when you’ve been telling him that for the last two years. It was just understanding how to navigate in that space and coexist and still thrive, and knowing you’re going to have to work at least five times as hard and not be afraid to be labeled as a bitch just because you were using your voice.”

Like many New Yorkers looking to discover their own personal identities in the ’80s, Walker was drawn to Dapper Dan’s shop in Harlem. Coming home from the Apollo Theater one night, she had an epiphany: Why wasn’t there a Brooklyn version of what was occurring Uptown?

She put her plan into motion. Utilizing a shoestring budget, sewing machines running nonstop out of a room in her house, and an unwavering belief that Hip-Hop culture was not a fad, Walker began crafting bespoke pieces.

“We surrounded ourselves with people who were in the fashion business and knew more than us from the beginning,” she says. “We knew the culture, they had the formula for the blueprint, and so those two things created a perfect storm to keep building. The tribe was the third part of the equation, which was actually our family, consumers, and people that loved Hip-Hop. We were able to combine all those three things to create Fashion in Effect, my first shop in Brooklyn.”

The shop on Greene Avenue was distinctly hers. The one-time butcher store still had huge freezers in which Walker kept fabrics. Customers entered through a little wooden door with a glass window, and everyone tagged their name on the wall. In the middle of the tagged wall was an image of a huge dog with an open mouth full of gold teeth and a clock that read, “Don’t believe the hype.” The shop was Hip-Hop personified with one-of-a-kind pieces that were in high-demand.

“We were doing all custom-made products at that time, one of one,” she says. “You could get anything you wanted made there, so we were doing everything from Easter outfits to sequin gowns to tuxedos to the big Nike sign with the velour sweat suits and leather collars.”

Walker eventually realized that while the one-offs were popular, it wasn’t a viable long-term business. She wanted to create something that could scale along with the growth of Hip-Hop. Walker Wear was officially born in 1990, ready to cater to the needs of artists like Run-D.M.C., MC Lyte, The Notorious B.I.G., EPMD, and 2Pac.

“The customers were asking me for bigger pockets, deeper pockets, more legroom, lower crotches, and more room to fit their Timbs in,” she says.

Walker first met Tupac when he was a roadie for Digital Underground. They formed an almost immediate connection based on their shared experiences on both the East and West coasts. Tupac eventually trusted her enough to begin sharing what would be the seeds of his debut album, 2Pacalypse Now. From there, he championed her for music video styling and specific pieces for the film Above the Rim.

“I think as you build relationships, you build trust,” she says. “And we just got closer as friends. He was very proactive about inclusivity for us and in us being in the conversation and trying to lift up his people.”

One of Walker’s most impactful pieces was her French-terry hockey jerseys. While the sport was decidedly un-Hip-Hop, the idea of playing in spaces where minorities didn’t typically prosper added to her enthusiasm to create the design.

“A lot of our stuff’s based on that,” Walker admits. “You want us out the door, we’re going to show you how to flip it and not pay you a royalty.”

While 2Pac is best remembered for his musical contributions to society, his willingness to use his platform to build up the Black community, specifically Black designers, can’t be overstated. 

“I’ve seen all of that — the crack babies, what we had to go through, losing everything, being poor, and getting beat down,” 2Pac said in the book Tupac: Resurrection, 1971-1996. “All of that. Being the person I am, I said no, no, no, no. I’m changing this.”

* Banner Image: Tupac at an Evening in Honour of Mikey Rourke at Nello’s (Photo by Lawrence Schwartzwald/Sygma via Getty Images)