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Daniel Day, aka Dapper Dan, and his wife, June Francis, (center) with their grandson Jibri Loving; Jibri’s son, Roman Loving; Day and June’s grandson Akil Loving; and their daughter Danique Day (from left). Jibri wears a Gucci sweater and shirt. Roman wears Dapper Dan Atelier clothing and bib. Day wears a Gucci blazer, shirt, pants, sunglasses, ascot, scarf, and shoes. Akil wears Gucci pants, shoes, and jewelry. Danique wears a Dapper Dan Atelier jacket and pants; Gucci boots. All other clothing and accessories their own.

Photograph by Jeff Henrikson. Photography Assistants: Jordan Zuppa, Austin Perrota. Still life Images shot on location at The Plaza, New York.

For our 2019 'Friends and Family' issue, we asked eight families—from multigenerational clans to collaborators who lean on each other like kin—to share what they’re giving and asking for this holiday season. Contributing editor Karin Nelson sat down with each group to paint a picture of their relationships and what they're getting up to this year.

The legendary fashion designer Daniel Day, aka Dapper Dan, grew up “dirt poor,” one of seven children in an apartment in Harlem. As he describes in his best-selling memoir, Dapper Dan: Made in Harlem (Random House), he was a dice-game hustler and a drug dealer and user—but through it all he remained a family man. All told, he fathered eight kids with seven women; two of them are with his wife of 51 years, June Francis. “Part of the reason I hustled so hard was so I could provide for them in ways that my parents hadn’t been able to for me,” he writes in the book, which is being adapted into a biopic by the actor and producer Jerrod Carmichael. Day opened his first shop in 1982 with money he had made from forging credit cards, and started screen-printing luxury logos onto his own designs, which became a huge hit with hip-hop artists. His shop was open 24 hours a day, seven days a week—the only time he closed it was for his father’s funeral—until the feds shut it down for trademark infringement, in 1992. In partnership with Gucci, he reopened two years ago, and now works alongside his son Jelani and daughter Danique. “They’re helping me take things to another level,” he says. “I wasn’t ready for the electronic age. I did everything out of pocket.” His grandson Akil Loving has also come on board as a designer, and with Day’s 12 other grandkids, as well as four great-grandchildren, his business is on its way to becoming a family empire. “The life I’m living now is totally amazing to me,” he says. “To come out of the streets and be here…I never imagined having such a structured life.”

Werkstätte Carl Auböck home accessories from Stillfried Wien, $117–$403, stillfried.com.

Photograph by Rob Kulisek; Set Design by Kate Atkinson.

Gucci armchair from Dover Street Market, $5,500, 646.837.7750.

Photograph by Rob Kulisek; Set Design by Kate Atkinson.

Brioni dinner jacket, $7,200, brioni.com.

Photograph by Rob Kulisek; Set Design by Kate Atkinson.

L’Objet Haas Lukas soup monster tureen, $1,100, l-objet.com.

Photograph by Rob Kulisek; Set Design by Kate Atkinson.

Francesco Maglia umbrella, $425, mrporter.com.

Photograph by Rob Kulisek; Set Design by Kate Atkinson.

Charvet shirt, $495, mrporter.com.

Photograph by Rob Kulisek; Set Design by Kate Atkinson.

Castro Smith rings, $1,522–$2,920 each, castrosmith.com.

Photograph by Rob Kulisek; Set Design by Kate Atkinson.

Nick Olsen for de Gournay dinner plate, $867, degournay.com.

Photograph by Rob Kulisek; Set Design by Kate Atkinson.

Vitamix Smart System blender, $650, vitamix.com.

Photograph by Rob Kulisek; Set Design by Kate Atkinson.

Brunello Cucinelli loafers, $825, 212.334.1010; Best Made Co. socks, $32 per pair, bestmadeco.com.

Photograph by Rob Kulisek; Set Design by Kate Atkinson.

Fferrone decanter, $220, and glasses, $180–$200 per pair, fferronedesign.com.

Photograph by Rob Kulisek; Set Design by Kate Atkinson.

Dapper Dan: Made in Harlem, Daniel R. Day (Random House), $28, randomhouse.com.

Photograph by Rob Kulisek; Set Design by Kate Atkinson.