When the clock struck midnight in Harlem, the activity outside of Dapper Dan’s atelier at 38 E. 125th Street would start to pick up.

The hustlers of the era were coming to get custom gear they planned to wear at clubs like Sal Abbatiello’s Disco Fever in the Bronx. As Hip-Hop culture grew in popularity, artists of the era like Eric B., Rakim, Run-D.M.C., LL COOL J, and Roxanne Shanté were amongst those waiting to pass through the entryway, which often boasted a $10,000 jacket, or $20,000 coat-and-hat combo.

While most store owners would have been delighted to service such an eclectic cross section of New Yorkers, Dapper Dan knew that he could better rely on those getting money on the streets — like James Jackson and Alberto Martinez — than those rocking the mic.

“There was no money in rap, so I wasn’t focused on the rappers,” he wrote in his memoir. “I didn’t care if they stayed outside or worked up the nerve to come in. I had a business to run.”

It had been men like Jackson and Martinez who prompted him to first ask the question of whether he could he take leather goods from brands like Gucci and Louis Vuitton and repurpose them into silhouettes that hustlers wanted to wear. When he acted on it, he forever changed the landscape of New York City fashion.

As Roxanne Shanté was igniting the “Roxanne Wars” of the era, business was also booming for Dapper Dan. Naturally, the teenage MC made it a priority to shop at his store, where she could cop one-of-a-kind counterfeits of the trendiest upmarket brands of the day, including Gucci, Fendi, Louis Vuitton, and MCM. For hustlers, it projected a sense of upscale ruggedness. For Shanté, it gave her the ability to cultivate the perfect blend of femininity and unattainability while “Roxanne’s Revenge” exploded across the radio waves.

“If you felt that you are one of a kind — that you are an original — then you needed to have a Dapper Dan in order to co-sign that,” Shanté says.

Shanté vividly recalls the energy of those midnight escapades. Hustlers, shot callers, MCs, and other people on the precipice of greatness were all shoulder to shoulder waiting underneath Dapper Dan’s yellow awning. The men were freshly shaved. The women’s dresses were tight and left very little to the imagination. They’d all watch Dan’s lanky frame glide down the block to unlock the door.

Dapper Dan didn’t hold court with everyone, but if you were special, or were a longtime customer, he’d make it a point to spark up a conversation. Shanté — only 14 years old at the time — was amongst those he’d acknowledge directly. It was like the Gucci-laced Willy Wonka telling you that he liked your flavor.

“I’m standing there waiting, and when I got the greeting from Dap, he knew it was a co-sign for everybody else to see,” she says.

Dapper Dan made it a point to package everything in a black zip bag so that other people waiting in line couldn’t sneak a peek at his latest creation. Just like with MCs, the fashion game of the mid ’80s was about one-upmanship. Thus, his entire business revolved around secrecy. Shanté recalls mid-day fittings where prying eyes were always kept to the minimum.

“The store was never crowded because he never let a whole bunch of people in at one time,” Shanté says. “You don’t want somebody to bite your style.”

When the steady rhythm of the sewing machine quieted, it meant that a piece was finally finished. Shanté would head to the club in her custom Dapper Dan leather. Her performance usually started between 2 a.m. and 4 a.m. It’s a time of the night she jokingly refers to as the “cocaine hour” because it was the party drug of the era — and seemingly everyone was using a little “marching powder” to keep the party rolling until the sun came up.

While Hip-Hop was — and to a certain extent still is — a boys’ club, Shanté was able to add a sense of femininity to her style by mixing Dapper Dan, the Shirt Kings jackets, cut-off shorts, cashmere sweaters, and gold door-knocker earrings from her jeweler on 47th Street. She was equal parts aspirational and approachable.

“I would say I had my own personal style,” Shanté admits.

As time went on, Hip-Hop could be heard thumping from Dapper Dan’s shop at all hours of the day and night. The hustlers liked the music, Dapper Dan liked their business, and teenagers like Roxanne Shanté — who was becoming rap royalty — knew that a Gucci jacket could take her to the next level.

* Banner Image: Roxanne Shante wearing an outfit by Dapper Dan / Photo by Michael Ochs Archives/Getty Images