Countless young girls-turned-grown-women cherish memories of raiding their grandmother’s closet, draping themselves in her pearls, tiptoeing in her “good” heels, and securing her church hats above their braided and beaded heads. But how many can say they’ve had the chance to repay the favor, dressing their grandmothers in contemporary styles pulled directly from their own wardrobes? This is the story of one such girl. Meet Diana “Dee” Kaumba, the stylist taking social media by storm with images of the family matriarch dressed down in designer threads.
Margaret Chola. Image: courtesy of Diana Kaumba.
Perhaps you’ve come across the photos before. Margaret Chola sits regally or is sometimes posed standing wearing Dolce and Gabbana dresses, Adidas track suits, Dior shades, and layers upon layers of bold and chunky accessories, an aesthetic that feels both current and reminiscent of flashy eighties styling. She’s even occasionally photographed holding a Razr phone, a Y2K relic straight out of Dee’s fashion archive.
While many of us may occasionally run to Pinterest to piece together new looks, Dee tells EBONY that styling is something she’s always had a natural knack for. The stylist recalls her father, a former UN diplomat in Zimbabwe, donning custom suits by designers he would have flown in from as far away as Hong Kong. She credits him for her love of fashion. As a teen, Dee spent the majority of her allowance on magazines and carried this passion into her adult life as she moved to New York City in 2002. Upon discovering the treasure trove that is the newsstand—a Big Apple staple she alternatively dubbed as “fashion heaven”—Dee soon realized that styling wasn’t just a hobby but a career path for some of the most successful entrepreneurs in the world. Having studied journalism in college, where she also learned to thrift and DIY her gear, Dee used the newly launched Instagram to start her own digital version of the glossies she so loved.
Drawing inspiration from the city’s vibrant streets and everyday life, Dee began styling herself, modeling her own looks, and sharing fashion-forward images she came across online. Her Instagram account @thevintagepoint quickly amassed tens of thousands of followers, some of whom began inquiring about styling services. And though she was pleased by the outpouring of support for her new endeavor, it wasn’t until Dee discovered professional stylist Rachel Zoe through her 2000s era reality TV show, The Rachel Zoe Project, that Dee began to understand fashion as a business, and just how she could take her place within the industry. In the years that followed, Dee built her styling business from the ground up, one client at a time. But just as her career was taking off, tragedy struck her personal life. During the peak of Covid, Dee’s father fell ill, and she became his caretaker. When he eventually passed due to kidney failure, Dee saw to it that he returned home to Zambia for his burial. She also began attending to the land that her father had left behind for her and her three siblings.
After her father’s passing, Dee felt the need to return home with more frequency. To achieve this and help her grieve, Dee began designing a small villa on her share of the property where she would open a vintage showroom with all of her wardrobe findings throughout the years. Soon after, she started receiving calls from Zambian celebrities for styling services. She continued to serve them from her own wardrobe, traveling back and forth from New York to Zambia on hired gigs. During one trip, while spending some family time on the farm, Dee decided it would be fun to have her and her grandmother switch clothes and have her photographer snap a few pictures. The stylist had the photos edited and posted them to her Instagram, not thinking much of it. But as fate would have it, the post went viral.
Margaret Chola. Image: courtesy of Diana Kaumba.
After initially going viral in 2022 thanks to a repost from the fashion icon herself, Erykah Badu, Dee set out to turn the mini moment into a collection of images she calls “The Granny Series,” the first Instagram post of which garnered 1,000 likes in ten minutes. It’s easy to understand the appeal of these photos. Major publications often fly entire teams to exotic locations with natural, color-saturated backdrops, aiming to capture images like those featured on the @legendary_glamma Insta. For Dee and her family, though, it’s just another day on the farm—moving from corner to corner across her father’s land, armed with only a single camera and the sun.
Though our social feeds may be flooded with beautiful AI imagery of Black elders in historic scenes in afro-futurist fashions, these productions are the real deal in real time. However, as much as Chola and the Granny series makes a case for disregarding age in mainstream model booking, the truth is that Dee and her family don’t actually know how old she is. However, there are some close guesses—placing her somewhere in her mid-eighties—based on the age of her children and the age she thinks she was when she gave birth. Despite this uncertainty, Chola tells her granddaughter that she once again feels she has a purpose in life. She’s a paid, working model, after all. And while she is handsomely compensated by her granddaughter and other clients (including Apple for a recent iPhone 16 ad in Zambia), Dee says that her preferred payments include handsome offerings of juice and chicken, favorites of the matriarch.
As far as what Dee has to say about the exclusion of models over a certain age in the fashion industry, “ageism is old,” the stylist shared. And while Dee’s stance might be influenced by her desire to maintain her status as the favorite grandchild, she hopes to shift the fashion culture for good.
