This upcoming Sunday marks another Mother’s Day. But as much as everybody loves a great mommy-and-me fashion moment, grandmothers are worthy of their own recognition. After all, a quick gander at Hollywood’s grandmothers reveals that we have many to thank for rewriting the rules of what it means to master ageless personal style. Granny chic of all kinds has continued to show up on the runways at Gucci, including everything from oversize glasses and patterned twinsets to mink coats. And if Grandma can play muse to directional designers like Alessandro Michele, then it’s well worth taking a look at the real-life style notes ahead of Sunday.
Consider Doria Ragland, who became a grandmother last year when her daughter Meghan Markle and Prince Harry welcomed their first son, Archie. Well before becoming a grandparent, Ragland showcased a polished sense of style—especially when attending the couple's royal wedding back in 2018, dressed in a mint green dress and coat by Oscar de la Renta and a white fascinator hat. Since becoming a grandmother, she's continued that refined aesthetic.
Susan Saradon is another prime example of a grandmother with exceptional style. The actress played a washed-up Bette Davis in the FX hit series Feud, and yet, her wardrobe spans decades with ease. Case in point: the gold metallic Dr. Martens–looking boots she wore with a flame red jumpsuit on the red carpet in February 2017—a moment that proved her innate cool and recalled the street style shoe championed by the likes of Gigi and Bella Hadid. Also having fun with footwear is Vanessa Redgrave, who recently wore a menswear-inspired tuxedo with Gucci loafers—the most It of It shoes—to receive the Icon Award from British Harper’s Bazaar, supported by her daughter Joely Richardson and granddaughter Daisy Bevan.
Even accessories frequently associated with grandmothers can look surprisingly hip, as evidenced by Bianca Jagger. When Jagger wed Rolling Stones frontman Mick Jagger in 1971, she broke tradition by wearing a scene-stealing all-white suit, and she’s continued to take a trailblazing approach to dressing since. Now, she styles her suiting with badass jewel-encrusted canes and blacked-out sunglasses worn with a chain-link, granny-chic cord. Perhaps the ultimate add-on, though, is a younger man, as demonstrated by Kris Jenner. The grand-momager has been known to borrow clothes from daughter Kim Kardashian West and wear similar looks—like the glitter-flecked Balmain jacket and trousers she wore on a date night with Corey Gamble, a man more than 20 years her junior.
Carole Middleton also channeled her daughter Kate in a pretty blue sundress similar to the Jenny Packham frock the Duchess of Cambridge wore when she left the hospital after giving birth to Prince George. Proving the old adage “like mother, like daughter,” both Middletons elevated their ensembles with neutral patent-leather pumps. Diane von Furstenberg, on the other hand, took a subtler, though no less stylish, approach to twinning when she stepped out with granddaughter Talita, both sporting similar fur-embellished statement jackets from her brand, which popped against their coordinating all-black outfits underneath. Another fan of bold outerwear is Hillary Clinton: The grandmother of Charlotte and Aidan recently tried out a leather blazer bearing the same clean, classic lines as the Ralph Lauren suits she wore on the campaign trail. Pairing it with a printed blouse and a gold medallion for added swagger, Clinton proved that even the most rock ’n’ roll staples can be a hit at any age.
