Prior to establishing himself as one of the most influential New York clothiers of all time, Daniel Day made ends meet as a professional gambler in his home neighborhood of Harlem. His winnings extended not only to the craps tables he frequented but also those he coached around the city. A caveat to Day’s success was his exuberant style and gregariousness at the tables.
“They wanted to win me,” he explained to the New Yorker in 2013. “I wanted to win money. That’s the difference.”
After spending his early adult years gambling, Day began to feel disenfranchised with the way of living. In the early 70s, he traveled through Africa where he was inspired by a Liberian tailor skilled at suturing local garments into familiar American silhouettes. Upon returning to New York City, he began his career as a tailor and soon opened his own 24-hour clothing shop on 125th street near Madison Avenue. Initially, Day began buying leather Gucci garment bags whose texture and dimensions were suitable to be made into jackets. Once demand grew for the unique pieces emboldened by luxury logos, he began printing replicas on his own materials.
Looking back on the legal risk that might eventually come from lifting the luxury symbols, Day reminisced “I knew that from day one, but I’m a gambler.”
The Dapper Dan Boutique creations were priced similarly to the luxury pieces they were composed and inspired from. The exclusive nature of Day’s work side-stepped any notions that he was in the lane of bootleg dealing.
“I Africanized it,” he described. “Took it away from that, like, Madison Avenue look.”
After a pair of his jackets appeared on the cover of Eric B and Rakim’s “Paid In Full” album, the pricey Dapper Dan originals became a status symbol in the burgeoning world of New York hip-hop. LL Cool J, Big Danny Kane, KRS-One and others quickly became regular clients. At a time during the city’s crack cocaine epidemic when mobsters like Leroy Barnes were appearing on magazine covers, new money figures in the city’s underworld saw Day’s store as a place to offload cash while not dressing like an old white businessman.
Day's work also became associated with the growing underground world along the rise of crack cocaine and organized crime in 80s New York City. At the time, mobsters like Leroy Barnes, were appearing on magazine covers and the city's new-money figures were looking for a way to offload cash in buckets while simultaneously avoiding the traditional luxury menswear staples that made them look like old white businessmen.
In 1998, Mike Tyson, a regular client, paid a late-night visit to the boutique to check on a custom order he had placed. Mitch Green, a New York-based boxer who had recently lost a 10-round main card fight to Tyson, caught wind of the visit and confronted his fellow boxer. A broken nose and shattered Rolls Royce window later and Dapper Dan’s Boutique was soon the backdrop to a mainstream news story. The spotlight shined a light on Day’s works, ultimately alerting the downtown brands he was co-opting to the ordeal.
Under trademark scrutiny and legal pressure, Day eventually closed Dapper Dan Boutique in 1992. Prior to shuttering, the designer had outfitted Olympic Gold Medalist Dianne Dixon with a recognizable Louis Vuitton-flipped fur puffer coat. Nearly 3 decades later, the coat was redone by Gucci creative director Alessandro Michele. The brand initially drew backlish for ripping the look but quickly released a statement declaring the similarities as an “homage”. Michele revealed at the opportunity to work with Day and Gucci soon tapped the legendary New Yorker for a collaboration. Still living in Harlem, the legendary designer released his official Gucci capsule the following year.