The Legend of Dapper Dan, Hip-Hop’s Most Iconic Tailor

You’ve heard the name before. Most of your favorite rappers and celebrities rocked his designs during the peak of Hip-Hop’s Golden Age. But there’s more than what meets the eye when it comes down to Hip-Hop’s most iconic tailor and designer. From his humble beginnings growing up on 129th Street and Lexington Ave. in Harlem, Daniel “Dapper Dan” Day has without a doubt molded the way Hip-Hop and fashion have intertwined. Long before the days of high-end designer brands co-signing rappers to wear their clothes; Dapper Dan was making identical custom clothing for a fraction of the cost for the likes of Salt-N-Pepa, Eric B. & Rakim, and even Mike Tyson just to name a few.

Being one of seven children, Dapper Dan knew what it was like to grow up and not have much. “My sense of style came from having holes in my shoes,” Mr. Day said in an interview with The New York Times. “I was in third grade, and I would put cardboard and paper in the bottom of my shoes, but it got to the point where the soles were just gone. I just couldn’t take it anymore. I came home from church one Sunday and told my mother: ‘Ma, my feet are killing me. They hurt so bad.’ I had tears in my eyes. The next day, my older brother Cary said: ‘Come on. We’re going to the Goodwill on 124th Street.’ We got there, and Cary asked me, ‘You see anything you like?’ I picked out a nice pair of shoes on the rack and tried them on. Cary asked me, ‘How do they feel?’ I told him, ‘They feel good.’”

As he got older, Mr. Day also realized how clothes were aligned with social status, as he would get teased about only getting shoes when his mother won the lottery. This became one of the reasons as to why Mr. Day became a tailor. Although, this wasn’t his intended career path, that all changed after being selected to go on an apprentice trip to Africa in 1968 for a program sponsored by Columbia University and the Urban League. It was that experience that ultimately led Mr. Day to realize that becoming a clothier was his calling, and there was no better place than to open up shop in his native of Harlem.

The original Dapper Dan’s Boutique, circa 1980s.

By 1982, Dapper Dan’s Boutique was open for business. Before Mr. Day had opened up shop, he began selling clothes out of his car. The clothes were purchased from “boosters”, people who would steal clothes from department stores and resell them. He would later end up building enough capital to start selling leather and furs, but merchants refused to sell to him. Of course, Mr. Day found a way with the help of Fred The Furrier, his brother Harold, and son Andrew Marc Schwartz, creator of the Andrew Marc label.

From there, Mr. Day began to sell Andrew Marc jackets with possum lining for $800 a pop, much less than a local competitor who was selling the jackets for $1200. After a demand to stop selling the merchandise to Mr. Day and a compromise to remove the brand’s name from the jackets, there was a realization of the importance of brand names.

Mr. Day had began to hire tailors from all over the city to help him create his vision of seeing designer logos and patterns as entire outfits. His boutique often stayed open 24/7, with drug dealers taking Polaroids of their latest pick-ups from Dapper Dan’s. Word traveled of Mr. Day’s designs all over the country, from Detroit to LA and even closer cities like Philadelphia. Mr. Day’s work became a staple in Hip-Hop culture, with Mr. Day designing Eric B. and Rakim’s outfits for the classic album, “Paid In Full”.

Pictured (from top left): Eric B. & Rakim, Salt N Pepa, Mike Tyson, and LL Cool J with Dapper Dan.

By the mid 1980’s, Mr. Day had incorporated brands such as Louis Vuitton, MCM, Fendi, and Gucci into unique designs and outfits. Ironically, the latter of the high-end brands sparked controversy after revealing one of the outfits from their Spring/Summer 2018 line. The jacket, sporting a fur vest with puffy arm sleeves bearing the double-G monogram, identical to a Dapper Dan design with the Louis Vuitton-print monogram from 1986. Gucci has since reached out to Mr. Day about the design, and saluted his work in an Instagram post.

Though the days of Dapper Dan’s Boutique are long gone, as the boutique closed its doors in 1992; the lasting impact of how Mr. Day changed the course of Hip-Hop’s fashion has remained timeless. From doing speaking engagements about his designs in their heyday, to personally answering questions on his blog, Mr. Day has remained equally as timeless as his designs, but more importantly, his impact.

Be sure to catch more on Hip-Hop fashion at the 13th Annual Brooklyn Hip-Hop Festival’s Hip-Hop Institute on July 12th at Medgar Evers College.