In 1987, a streetwise d.j. from Queens named Eric Barrier released an album with an eerily mature teen-age rapper from Long Island named William Griffin. They called themselves Eric B. & Rakim (Griffin had adopted an Arabic name after joining an offshoot of the Nation of Islam), and they called the album “Paid in Full.” Its cover was meant to provide proof of the boast: the two men are photographed holding fans of cash, superimposed on a green-tinted image of giant bills. Their fingers are covered in gold rings; around each man’s neck is a gold chain that looks thick enough to suspend a bridge.

Even so, most people who see the cover will find their eyes drawn to the matching leather outfits that the two are wearing. The jackets dominate the frame, and, on the back cover, one of them serves as a backdrop for an impressive still-life composed of jewelry, money, and a personal check signed by Ronald Reagan. The sleeves and torso are black, but the collar and shoulders and wrists and pockets are white leather, decorated with a tiny logo print: a series of double “G”s, the second one inverted, each pair separated from its diagonal neighbor by a black dot. If you look closely at the black leather, you can see the same pattern there, black on black. It’s a Gucci logo, and on the chest is another one: a pair of fist-size interlocking “G”s.

“Paid in Full” was a hit, and a turning point: its imaginative samples inspired hip-hop producers to broaden their palettes, its sinuous rhymes inspired rappers to stretch out their verses, and its audacious cover helped convince rivals and fans that hip-hop fashion might mean something more luxurious than a T-shirt or a track suit. Of course, fans hoping to buy their own logo-print Gucci jackets wouldn’t have met with much success at the company’s Manhattan boutique, at Fifth Avenue and Fifty-fourth Street, which sold mostly handbags and wallets. But within the emerging hip-hop industry the source of those outfits was an open secret: they came from a bustling shop seventy blocks north, in Harlem, called Dapper Dan’s Boutique.

By the time “Paid in Full” was released, the boutique was already a success. Its storefront, on 125th Street, was open twenty-four hours a day, providing custom tailoring and name-brand cachet—Gucci, Fendi, Louis Vuitton—to anyone who could afford the prices, which ranged from a few hundred dollars to a few thousand. At Dapper Dan’s, “made to order” didn’t always mean “one of a kind”: customers often requested copies of other customers’ clothes, causing the best-loved pieces to replicate and spread outward from celebrities to regular folks—albeit regular folks willing to spend an irregular amount on luxury clothing of dubious provenance. Many of the celebrities were rappers and athletes: LL Cool J, Big Daddy Kane, and KRS-One were regular clients, and so were Mike Tyson and the basketball star Walter Berry. Major drug dealers counted as celebrities, too, like Alberto Martinez, known as Alpo, whose purchases included a beautiful tan-and-brown Louis Vuitton logo-print snorkel parka with a fox-fur hood. (It had cleverly designed double pockets in the front, just in case the wearer had something he might want to store separately or discard quickly.) Martinez was arrested in 1991 and convicted on multiple charges of homicide, but the parka, commonly known as the Alpo Coat, became one of the boutique’s signature creations—a crack-era classic.

It seems possible that, in the nineteen-eighties, Dapper Dan was the most influential haberdasher in the city. His work presaged both the rise of the hip-hop fashion industry and the reinvention of Europe’s luxury design houses. June Ambrose, a stylist who made her name by bridging hip-hop and high fashion, grew up in the Bronx, and she remembers marvelling at Dapper Dan’s rogue creations, which allowed his new-money clients to festoon themselves in old-money symbols. “It was like wearing a Rolls-Royce on your back—it was so cocky,” she says. “It was luxury on steroids. You didn’t have to say this jacket was ten thousand dollars. It just looked like it was ten thousand dollars.”

In the convivial atmosphere of the shop, Dapper Dan was a friendly but serious presence. He took measurements and drew up designs, leaving most of the sewing and cutting to African tailors, mostly Senegalese, who worked in shifts upstairs from the shop, sometimes a dozen at a time. Dapper Dan wielded several different kinds of authority, depending on whom he was talking to: he could be a self-taught philosopher, a refined couturier, a gruff salesman (no discounts, no matter what), or a local guy who found subtle ways to remind people that he knew lots of other local guys, not all of them quite so refined as him. He cultivated a sense of mystery about the trademarked materials he used, and about himself. Mike Tyson remembers him as “a beautiful guy,” with a slightly anomalous sense of propriety. “He conducted himself real dignified,” Tyson says. “You know, them African guys are dignified and shit—I thought Dapper Dan was African.”

Dapper Dan’s Boutique closed in 1992—its demise hastened, indirectly, by Tyson’s patronage. In the two decades since then, Dapper Dan has lived on mainly in the mythology of hip-hop: through old album covers and magazine snapshots, as well as occasional acknowledgment on rap records. Fat Joe, a longtime customer, once declared, in a song, “You can ask Dapper Dan, Who was the man?” Jay-Z, who largely missed out on the Dapper Dan era, offered a more equivocal salute to those famous Gucci jackets: “Wear a G on my chest—I don’t need Dapper Dan.”

It was doubly startling, then, when Dapper Dan reappeared, a few months ago, in a five-minute biographical video that was posted on Life + Times, Jay-Z’s life-style Web site. He is sixty-eight now, though he looks at least ten years younger: he is skinny and bald and dark—it’s not hard to see why Tyson thought he was an African immigrant. In fact, he was born in Harlem, the son of a homemaker and her husband, a civil servant who had moved north from Virginia in 1910. Dapper Dan’s real name is Daniel Day, and he still lives in Harlem, in a brownstone a few blocks from 125th Street. He still dresses, too, like an uptown dandy. One day, not long after the video surfaced, he answered the door wearing a slim-fitting black shirt with small red polka dots and a white collar and cuffs; gold cufflinks matched the gold clip that held down his red tie. In person, his natural exuberance often seems to be doing battle with his learned wariness, both of which have served him well. He has a tendency to tell even the most benign story in a near-whisper, which makes the sudden explosions of laughter more dramatic.

Day grew up poor, the youngest of four brothers, and poverty magnified his innate interest in clothes; he used pieces of linoleum to cover the holes in the soles of his shoes. He still remembers a friend’s casual but devastating response the day his mother bought him a new pair: “Oh, look, they must have hit the number.” The friend was right—the Day boys got new clothes only when their mother’s lucky number, 150, came up in the local lottery. As a teen-ager, he became an accomplished shoplifter (pillaging department stores like Alexander’s and Hearns), and therefore a stylish dresser, but it never occurred to him to study fashion—instead, he dropped out of school. He was once a budding kingpin, the president of the Sportsmen Tots, the youth division of a fearsome gang. But by the time he reached his late teens he had become something of an idealist, a believer in the virtues of total sobriety, even though most of his friends were confirmed skeptics. Eventually, Day found his way to the Urban League, which offered a program to instill pride and discipline in wayward young black and Latino men by sending them to Africa for the summer. Day still has a copy of a test he took as a prerequisite, which reflects the political vision of the trip’s sponsors. One question asked candidates to imagine themselves as leaders of a small African country battling starvation: would they accept a loan from a larger country if it came with conditions? Day’s answer, written in soft pencil, is firm: “I would reject it because African unity means more than the lives of thousands it mean the lives of 10 of millions.” Underneath, one of the instructors wrote, in red ballpoint, “Excellent!!”