It was a mentor on the gambling circuit in Harlem, New York, who gave Daniel Day the moniker that would make him famous. Day was just 13, but had revealed himself to be not only a better craps player than his guide, who was the original Dapper Dan, but also a better dresser. So it came to be that Day was christened “the new Dapper Dan”.
It wouldn’t be until decades later that Day would truly make his name. Dapper Dan’s Boutique, the legendary Harlem couturier he opened in 1982, kitted out local gamblers and gangsters, then later hip-hop stars and athletes such as Mike Tyson, Bobby Brown and Salt-N-Pepa. His custom pieces repurposed logos from the fashion houses that had overlooked black clientele. A pioneer in luxury streetwear, Day screenprinted the monograms of Gucci, Louis Vuitton, MCM and Fendi on to premium leathers to create silhouettes synonymous with early hip-hop style: tracksuits, bomber jackets, baseball and kufi caps. In the process he became a pariah of the fashion industry – and to this day, now aged 76, still one of its great influencers.
Day was born into poverty in East Harlem in 1944. He remembers when horse-drawn carriages lined the streets of Manhattan. His parents arrived during the Great Migration, which saw millions of African Americans flee the more overtly racist south in the early 20th century. “Even though we had a class that was capable of moving out [of Harlem], segregation wouldn’t allow that,” he says. “That’s why the Harlem renaissance – all these dynamic writers and poets – they were there because they had to be there.”
His mother was a homemaker and his father worked three jobs to make ends meet. Day and his three brothers and three sisters would go down with holes in their shoes to the nearby Harlem river to build models from the mud because they couldn’t afford toys. “We was very, very poor,” he says. “To compare it to anything you see today, it was like the favelas or Soweto.”
Shoe-shining was Day’s first adolescent “hustle”, quickly followed by gambling. “First thing that I learned in life was about the gospel,” he says. “The second was gambling.” He acquired the basics from his uncle, “Fishman Eddie”, who was a professional. But Day was also a keen reader and soon began devouring books on “percentages, law of probability and manipulation and sleight of hand”, and became, in his words, “very proficient at it”. At 13, he was earning thousands of dollars a day.
By high school, Day and one of his brothers had started using heroin – and in his early 20s, he was arrested for dealing drugs. He notes in his 2019 memoir, Dapper Dan: Made in Harlem, that had he been jailed today instead of in the late 60s, before harsh, discriminatory drug laws were implemented, he might have been imprisoned for a lifetime. Instead, he got one month and used prison as an opportunity to get clean, going cold turkey. “I was locked up with an older guy from my neighbourhood, Vic,” says Day. “And Vic says: ‘Listen, you know what you feel now? Well, it’s never getting worse than that.’ I learned that I could conquer these things.”
When Day left prison he began writing essays on Pan-Africanism in the late-60s progressive Harlem publication Forty Acres and a Mule. His mother was a Garveyite – an advocate for the black separatist movement led by the Jamaican activist Marcus Garvey. His father, who moved to Harlem alone in 1910 aged 12, was born just 35 years after the Emancipation Proclamation. His paternal grandfather was born a slave and later freed. “I developed a consciousness along those lines without really realising it, because I was constantly listening to my mom and dad talking about the trials and tribulations associated with being black,” he says.
His writing led to him touring Kenya, Uganda, Ethiopia, Egypt and Tanzania in 1968, as part of a programme sponsored by Columbia University and the civil rights organisation the National Urban League. Six years after his initial visit, he went back to Africa to see the famed Muhammad Ali v George Foreman “Rumble in the Jungle” fight in Kinshasa in what was then Zaire but is now the Democratic Republic of the Congo. The fight was postponed because Foreman had been injured while training, so Day travelled to Lagos, Nigeria and Monrovia in Liberia. There, he befriended a tailor who made him a suit from vivid local fabrics.
This west-African take on American style would serve as the primordial soup for his “Africanisation” of the designs of high-end European fashion houses. Day never made it to the boxing match – he spent all his money on more custom pieces and took a flight home. But what he had found was his calling. He returned to New York and became a clothier.
At first, for a few years, Day sold stolen designer goods out of the trunk of his car. When he set up his first boutique on 125th Street in Harlem in 1982, he kept it open 24 hours a day to cater to the schedules of his clientele: drug kingpins who had got rich on the crack cocaine boom, gangsters, professional boxers and rappers. At first, the boutique sold furs. But when the girlfriend of a drug dealer came in with a Louis Vuitton purse, and Day saw the faces in the store all turn to look at it, he realised that the power of fashion went beyond aesthetics. He went to his local library to study the origins of the Gucci and Fendi logos and their evolution from mere hallmarks to status symbols. He understood what wearing a designer logo meant to his customers and how it made them feel.
The first piece Day made was a jacket, which he trimmed with logo-printed canvas garment bags he had purchased from Gucci. The jacket was a hit after a client wore it to a party and everyone wanted to know where it came from, but Day met hurdles from the outset. Like his customers, he too was alienated by the overwhelmingly white fashion industry. Recalling his first trip to Louis Vuitton on Fifth Avenue, he describes the whole shop tensing up when he walked in. On other occasions, he was prohibited from buying goods from the stores. But he was undeterred; fashion, too, was a hustle.
Back then, the only items luxury fashion houses were producing with all-over logos were leather goods and accessories, so Day taught himself fabric and leather printing techniques to create his own textiles featuring the iconography of Louis Vuitton, Gucci and MCM. “Fortunately, I had been to Africa and knew that I could make the same things that [luxury fashion houses] rejected me for – and to make it better.”
Day’s offerings soon became preferable to the real thing. His bold prints were synonymous with the bombastic style and braggadocio that was beginning to typify hip-hop – and Day was creating designs for the cream of that scene: Big Daddy Kane, Eric B and Rakim, Run DMC, LL Cool J, Slick Rick. In the same way that sampling was rife in the music, so it was in hip-hop fashion: customised T-shirts and jackets were staples. Day’s ostentatious creations didn’t emulate, but rather amped up the luxury of existing labels, and he took to referring to them as “knock-ups” as opposed to “knock-offs”, saying he simply “blackenised” the brands. He cites the cash-poor, snappily dressed sapeurs of Congo, who adopted and adapted the fashion of French colonisers, donning three-piece designer suits and crocodile shoes despite their destitution. “That culture – that’s what happened to me,” Day says. “That’s why you saw Cadillacs pulling up to a dilapidated building in Harlem.”
Alongside race, class played a big part in how Day’s work was received. Middle-class black people showed the same level of disdain towards him as the white-dominated fashion houses or white Americans. “It took until last year for Ebony magazine to feature me,” he says. “Once you’ve been embraced by white people, people look at you differently, right?” Last year, he was named as one of Time magazine’s 100 Most Influential People.
Back in the 80s and 90s, even those of Day’s customers who might have been willing to brave the hostile environments of New York’s high-end fashion stores still struggled with finding suitable pieces. Ready-to-wear designer fashion was still relatively new (Louis Vuitton, for example, did not do a full collection until 1998) and the European sizing didn’t fit the broader build of the rappers and athletes who made up Day’s customer base. His designs catered to their specific needs: bullet-proof parkas for drug kingpins or jackets for gangsters that were fitted with extra-deep pockets to conceal weapons. “Fashion designers create from their mind, like poets and writers,” Day explains. “I feel more like a doctor – I have to make the patient feel good.”
Day’s growing success was a double-edged sword. By the late 80s, the boutique was being regularly raided by the police. In 1988, Day made national headlines when Mike Tyson and fellow boxer Mitch Green were photographed fighting outside the boutique, Tyson wearing one of Day’s “Fendi” jackets. Another raid followed – and the authorities seized not only equipment, but material and photos, which served as the only existing records of the pieces he made. In recent years, Day and his son – and brand manager – Jelani have begun trying to catalogue his surviving pieces. “Seems like at least once a week someone is popping up with an original Dapper Dan,” he says, laughing. “I know one guy’s got a collection I wish I could get, but he swears he’s not giving it up.”
There were more raids, and more close calls. When Day witnessed a drug dealer being kidnapped in his store, he was shot in the back and nearly died. In 1992, after a successful trademark infringement case from Fendi, Dapper Dan’s shut for good.
Day returned to selling on the streets, faux Chanel T-shirts to private customers. In the late 90s, he set up a smaller-scale, more discreet operation in the home he shared with his wife and their two kids. “I had to go back to taking the subway, bringing fabric uptown on the train,” he says. “I wasn’t gonna fall victim to the worst slave master ever – the ego. You don’t fall victim to that and you’ve made it.” He was still exiled by the mainstream, but flourished on the fringes as ever. In 1999, he began outfitting the undefeated boxer Floyd Mayweather Jr. His legacy was frequently referenced in rap lyrics by Jay-Z, Pusha T, Lil Wayne and Tyler, the Creator among others.
In 2017 came a turnaround in Day’s fortunes. When Gucci put a puff-sleeved mink bomber jacket emblazoned with the double G monogram down the catwalk, the piece’s similarity to a Dapper Dan jacket made for the Olympian track star Diane Dixon in 1989 was picked up on by social media users. The anger was palpable: Day’s business had been shut down after European luxury brands came after him for copyright infringement, only for one of those same luxury brands now to copy his work, uncredited. At the time, Gucci said the jacket was a “homage” to Day’s work.
And then something unprecedented happened: a collaboration. Gucci hired Day to design a capsule collection, and in 2018 it sponsored a new appointment-only atelier in Harlem in tribute to his original boutique. To him, it is a fitting remedy. “Cultural appropriation and cultural exchange breaks down to one thing: economics,” he says. “An exchange involves somebody getting something, for whatever it is they have. Appropriation means you ain’t getting nothing.”
While the collaboration has been largely celebrated, some have remained critical. “I describe what I did as coming up a black staircase, as opposed to what Naomi Campbell or [Vogue editor] André Leon Talley did, which was come up a white staircase,” he says. “I didn’t have any contact with the fashion industry until I got this partnership with Gucci. I didn’t even have any white friends or associates until four years ago.” He rubbishes cynicism about collaborating with brands as “Jim Crow economics”. “When you talk to people and they’re like: ‘We can do it ourselves. We had a black Wall Street’, I say: ‘We had a black Wall Street because we wasn’t allowed on [the other] Wall Street … We had no alternative but to sell to ourselves.’”
The racist belief that black people devalue luxury brands is gradually changing. The rapper Nicki Minaj launched a capsule line with Fendi last year; and after years of ignoring him, Gucci employed the rapper Gucci Mane to front a campaign. But fashion’s problem with race remains, as recent scandals can show. In 2018, a display of tchotchkes in the windows of a New York Prada boutique included one that looked like a Golliwog. When Gucci was forced to withdraw a balaclava polo neck jumper from its shops in 2019, after it was said to resemble blackface, Day summoned the company’s president and CEO, Marco Bizzarri, for a meeting in Harlem to hold the brand accountable. Luxury labels, he says, want fast access to black culture, often without truly trying to understand the meaning or history behind it.
“Even me, I feel corny sometimes because the culture is moving so fast,” he says. “Black American culture is so popular right now that they look for anything they can use, without studying the significance of what it is to use them.”
Day still lives in Harlem, of course; some of his new customers are second- and third-generation Dapper Dan devotees. The rapper ASAP Ferg, real name Darold Ferguson Jr, was mentored by Day, and his father, Darold Sr, worked at the boutique in its heyday.
Well into his eighth decade, Day is at ease with change, still reinventing himself. A much overdue biopic is in development at Sony, which he will executive produce. He has every intention of continuing to experiment with new hustles. “I don’t give a damn about failure,” he smiles. “I was born part of failure. We are the phoenix – all of us here in America, every black man, woman and child are part of the phoenix, still rising from those ashes. All my life is about getting knocked down and getting back up. I don’t care; it’s fun!”