The Harlem hustler once won $50,000 playing dice. He devised scams so ahead of their time that police didn’t even know what to charge him with.
And then Daniel R. Day came up with his greatest idea of all: Designing clothes that made a generation of rappers look like the gangsters they wanted to be.
He’s gone from prison to penthouses, partied with L.L. Cool J and peddled T-shirts on the street. “Dapper Dan: Made in Harlem” is his story, a gritty memoir in the style of Iceberg Slim’s “Pimp,” a streetwise adventure in “Super Fly” style.
Unlike those characters, though, Day didn’t abuse women, or dream of million-dollar coke deals. He just wanted to look fine, and live well. And to a kid from World War II-era Harlem, that meant cutting corners.
Until he saw he could make more money cutting fabric.
Day was born in 1944, and his memories are mostly sweet. He remembers a Harlem before housing projects, when every block felt like a neighborhood. Fathers held down three jobs, then cut loose on weekends. Mothers sat on stoops, shelling peas, and minding everybody’s business.
Life was still hard, though. Day remembers going hungry, and stuffing pieces of linoleum in his shoes, to patch the ragged soles.
But he also remembers seeing stylish black men, well-fed gentlemen in three-piece suits. They ran the numbers racket. And when drugs took hold in the 1950s, they ran that, too.
Little Danny loved their style.
He first picked up the Dapper Dan moniker in grade school, sporting creased jeans and polo shirts. He dressed to impress, and the tidy look not only earned him respect, but it also seemed to bring him luck, or at least an advantage.
His slick style and cool attitude helped him boost clothes from Alexander’s in the Bronx, where he walked in with empty shopping bags and walked out with sweaters. It helped in dice games, too. People looked at the well-dressed, icily calm teenager and figured he must have an edge.
Day did, too. Always a reader, he read every book on gambling the New York Public Library had. And, not surprisingly, he was good in math, which helped him calculate the odds.
The loaded dice he bought at a Midtown magic shop also gave him an edge.
Drugs, though, were a different game. Day first started sniffing heroin in junior high. By the time he dropped out of high school, he was using and selling full-time. Arrests followed.
Prison, rehab, and a newfound interest in religion, metaphysics and spirituality straightened him out. But not so much that he actually went straight.
Instead, he went back to the streets and back to the dice. He made thousands of dollars a day. He bought a brownstone, sent his children to private school.
That last expense was significant. Eventually, Day had eight kids with seven different women. “I consider sex a deeply spiritual and meaningful act,” he explains. And he always searched for meaning.
Gambling was dangerous, though. Only gangsters could afford the stakes Day liked. He often found himself in after-hours clubs, rolling dice with lethal guys who worked for heroin kingpins like Nicky Barnes and Frank Lucas.
One night, Day was up over $50,000. He also noticed the mood in the room had changed. Suddenly he didn’t like the way people were looking at him.
He casually put his winnings in his pocket, then slapped another $500 down. “Hold this bet for me, I gotta take a leak,” he said.
Instead, he ran.
He found out later the gangsters had decided he was part of a rival gang and had planned to kill him and dump his body.
There had to be an easier illegitimate way to make money.
Day found it almost by accident. A thief gave him some stolen credit cards to settle a debt. Day tried that scam for a while, then figured out a better scheme: He would make his own credit cards.
Day got a friend to steal an embossing machine that made plastic employee IDs. He collected old charge receipts from the trash and slapped legitimate numbers on new, fake cards
Walk into a bank with one, and you could walk out with a cash advance.
It was illegal. Except technically, Day says, it wasn’t.
It was a crime to steal credit cards, of course. But there wasn’t a law about appropriating credit card numbers. Even when they were nabbed, Day and his gang would always get the charges tossed.
Until finally, the feds got wise. Bills were proposed, and the day they became laws, Day threw his embossing machine in the East River. It was time, he declared, to go straight.
Straight into fashion.
Day had always loved clothes. Now, instead of shoplifting them, he decided to sell them. He found an empty storefront on 125th St. and started buying wholesale from Fred the Furrier. Day would sell mink coats to the pushers and pimps who loved the style but didn’t want to deal with a white storekeeper’s attitude.
Once Day had the gangsters buying, he started getting the folks who just wanted to look like them. Soon people like Eric B. & Rakim, and LL Cool J were all shopping. They didn’t just want furs; they wanted to be outfitted in designer jackets, suits, coats.
Seeing an opportunity, Day went down to the Louis Vuitton store on Fifth Ave. and bought an armful of their monogrammed garment bags. Then he took them back to his store, pulled out the stitches, and had a tailor turn them into suits.
Vuitton might not sell clothes. But now Dapper Dan did.
The look took off. Day expanded, buying equipment so he could dye the leather himself. Soon he was turning out entire wardrobes stamped with any designer logo anyone wanted.
You wanted your car upholstered with leather stamped LV? Sure. You wanted a bulletproof parka emblazoned with the Gucci double-Gs? Done.
His 24-hour-a-day boutique expanded and filled up with millionaire rappers and celebrity athletes. Russell Simmons came by to flirt with the salesgirls. Heavyweights Mike Tyson and Mitch Green got into a street fight in front. Dapper Dan’s clothes started showing up in MTV videos
They also started showing up on law enforcement’s radar.
Today, Day defends his work as cultural commentary, like Andy Warhol painting a Campbell’s soup can. The designers’ lawyers, however, saw it as theft. Day’s Fendi trench coats were knockoffs, they said, no different than counterfeit pocketbooks sold on Canal St.
He started getting raided regularly, whole racks of merchandise confiscated. His store was shut down. He survived by hawking t-shirts on the street, clothes out of his car.
Slowly, though, Day came back. Avoiding other people’s logos, he started doing custom designs for artists like Ghostface Killah, Busta Rhymes, and Aaliyah. Floyd Mayweather became a regular client. Fat Joe and Jay-Z name-checked him in songs.
Fashion critics took serious notice. His designs were featured at the Smithsonian, the Metropolitan, and MOMA. Finally, in 2017, he reopened his boutique — now in partnership with Gucci. The outlaw was finally, ultimately, legit.
And for Dapper Dan, that must be the weirdest happy ending of all.