How Family Lives On Through Fashion Heirlooms

The term “personal style” is a slightly misleading one, as if the way one gets dressed is a fixed, intractable quality they’re born with. The truth, though, is that while some people certainly possess a natural aptitude for wearing clothing with flair, it takes a lot of outside shaping to realize one’s full potential. Coming from a fashion-minded family helps a lot, as it means you’re surrounded by a treasure trove of interesting garments as well as intel on pulling them off. Case in point: Nicole Kidman’s daughter Sunday Rose looked amazing at the Met Ball a few weeks ago, but do you think she’d know how to work a Dior gown at age 17 without the help of her mom? Not likely.

Kit Keenan, a lifestyle influencer and the author of the cookbook In Good Taste, can’t remember a time when style wasn’t a defining force in her home. “Watching my mom get dressed in the morning was always a moment,” she says. As the daughter of prolific New York fashion designer Cynthia Rowley, she and her younger sister, Gigi Powers, learned the ins and outs of expressing themselves with clothes from the earliest age: which pieces worked with what, which rules to follow and which to break, how to alter any item to suit their needs. As she points out, a fashion perspective is something you craft for yourself out of myriad references throughout your life, but “growing up around someone with such a strong sense of style definitely makes you more aware of individuality.” To that end, she continues, her approach to pulling together outfits is “always in conversation with my mom, but also entirely my own.”

Taking valuable style cues from one’s predecessors is, of course, nothing new. Women have been borrowing from their mothers’, grandmothers’, and aunties’ closets since the beginning of time. The difference is that now, in the age of social media, many girls are taking to the internet to share the treasures and advice they’ve been surrounded by since birth — oftentimes bringing their family along for the ride. Meanwhile, a fresh wave of style-minded moms are documenting the ways their wardrobes are shifting through parenthood, and fostering love for fashion in their own children along the way.

Ahead, TZR has spoken to fashion and culture insiders from multiple generations for whom fashion is not just an interest, or even a passion, but a way of connecting with the other women in their families.

An Archival Bond

Throughout Kara Mendelsohn’s many decades working at mega-brands like Calvin Klein (Carolyn Bessette Kennedy was her coworker, NBD) and Michael Kors — as well as her own line, Cooper & Ella — she amassed quite the luxury clothing archive. “Each designer [in my closet is from] a different stage of my life,” she says. “My 20s, then 30s, and then 40s were all lived while at different design houses.”

This gold mine of vintage is something Mendelsohn’s daughter, influencer Ella Mendelsohn, 21, is more than happy to take advantage of now, both personally and professionally. She and her mother, who has recently pivoted to professional content creation as well, have turned the hand-me-down process into a shared video series in which Kara, 51, styles Ella in decades-old designs from her personal collection — complete with sage insider advice on how to pull off each item.

“It’s so funny because I’m carrying the bags my mom went out to dinners and partied with in NYC; I now do the same,” says the younger Mendelsohn, who loves reinventing a piece from over 20 years ago by combining it with new season designs. “I’ve even had fashion girls come up to me and ask if my bag is vintage Marc Jacobs, etc. I love that I can give my mom’s pieces a new life by styling them in a different way.”

Bonding over archival style — and high fashion in general — has not always been a part of the duo’s relationship. “When I was in middle school, all the girls were wearing Justice, and my mom refused to shop there,” Ella Mendelsohn recalls, noting she wore a lot of Zara and Bonpoint instead and “never felt on trend.” Much to her mother’s chagrin, she eventually shifted toward crop tops and sweatpants in high school. “I finally did a major closet purge and elevated my style [between the ages of 18 and 20],” she says. “Looking back, I can appreciate my mom’s advice and what she was trying to do — but back then I didn’t get it!”

A Reimagined Legacy

Olivia Galli, 28, always knew her grandmother — the late Joan Johnson, who founded Johnson Cosmetics with her husband, George — had a fabulous wardrobe. “Anytime I’d visit my grandmother, I would play hide-and-go-seek in her closet,” she remembers. “I’d see and admire all the clothes and try on her heels even though I was tiny. So [style] really just has always been part of my life.” But the photographer and model didn’t fully realize how big or special Johnson’s collection was until she began digging into near-endless boxes of styles her grandmother left to her: an opulent archive spanning Chanel bags, Dior jeans, and Jean Paul Gaultier outerwear, all of which she’s been unboxing and sharing through a series of buzzy online videos.

To her, these incredible pieces are both reminders of a person she loved dearly and clues to a side of Johnson she never really knew. “I recently visited my grandfather’s apartment in Chicago and was rummaging through this bin of photos and found all these pictures of my grandmother and her style,” she says, recalling that while she always knew her grandmother to be perfectly pulled together, she missed out on decades of dramatic outfits from before she was born. “I wish I was older, and I could have seen it all firsthand.”

At first, Galli was unsure how best to pay homage to the abundance of fashion riches she had received. Not everything fit her body properly or felt true to her personality. “I was mesmerized by my grandmother’s clothing, but then I’d try to wear it... and it was just not hitting,” she says, noting the push-pull she felt between giving each piece its proper due and exploring her own personal style — which, she points out, is a constant work in progress. Over the years, it’s gone from being quite formal (think pencil skirts, blazers, and button-downs) to far more experimental and playful; she loves pairing a more casual piece, or jeans or a T-shirt, with something more opulent, such as printed pants or an evening jacket.

“I look back at some of my old videos when I was starting out, and I’m like, ‘What is this outfit?’” she says. “[It wouldn’t be] properly tailored or make any sense. I think taking a step back and being able to wear one thing of my grandmother’s, but then the rest can be what I purchased myself, is a good balance between the two.” Case in point: a decades-old chocolate brown Chanel bag she shows off during her interview that works with just about everything — including her preferred off-duty combination of a relaxed Ralph Lauren teddy bear sweater and wide-leg jeans.

Like Mother, Like Daughters

Born in a tiny Midwest town to a scientist father and artist mother, NYC-based designer Cynthia Rowley, 67, says her childhood was imbued with “an unusual combination of creativity and inventiveness.” So it was only natural that she’d encourage her own daughters — cookbook author and entrepreneur Kit Keenan, 27, and influencer Gigi Powers, 21 — to experiment with fashion. Keenan says she has fond early memories of her mother encouraging them to dress with imagination. “For a full year, I wore my birthday crown to school, and on Gigi’s first day of kindergarten, she wore a Barbie life jacket,” she says. “There were never really any boundaries, and she always encouraged self-expression.”

These days, Keenan and Powers have established their own specific ways of getting dressed, but still constantly borrow from their mom. “We have a company archive full of decades-old runway and archival pieces they love to raid,” says Rowley. “My closet is unfortunately fair game too.” And while Rowley certainly has plenty of sentimental items stashed away, she doesn’t get too precious about allowing her girls to wear them however and wherever they want. “What I love about fashion is that it’s always evolving,” she says, pointing out that a closet can feel like a scrapbook of memories, and she enjoys sharing the stories behind each garment with her girls. “But more than anything, I’m excited to see how Kit and Gigi take some of my archival pieces and make them their own.”

One item in Rowley’s wardrobe that’s always in demand? “My mom has a pair of vintage Levi’s from when she was in high school that Gigi and I fight over to this day,” says Keenan. “They’re completely ripped and patched up, but somehow they have the perfect wash and fit. We’re constantly borrowing them from one another because they’re one of those pieces that just can’t be re-created.”

Future Heirlooms

Although Gina Bruno, 34, is best known for hosting the chef-centric interview show Campers as well as private dinners at her event space This Is Frank’s House, she’s also cultivated an artsy-cool minimalist look for all her professional appearances; think blousy tops, relaxed Bermuda shorts, and playful earrings. Her appreciation for a well-put-together outfit is something she hopes to hand down to her young daughter, Mars. It’s a bit of a shift from the dynamic she had with her own mother, who had excellent taste but preferred an understated look.

“You’re either someone who gives a sh*t about what you wear, or you’re not — that part is wired from the jump,” she says, noting that her mom is not a “fashion person,” but she has always been obsessed with clothes and the narratives you can create with them. So far, it seems that Mars might be following the same path. “She’s only 2 and already has strong opinions about what matches and what doesn’t,” says Bruno. “Nobody handed any of us that — we just have it!”

She may be a toddler, but Mars seems to have a strong penchant for purses. “I’m not a huge bag girl, but I have a few that I worked and saved for,” says Bruno. She’s been daydreaming about the styles her toddler might carry one day, and how she might style them. “It almost makes me want to buy one or two more from my wish list, so I can enjoy them for a moment and save them for her — really, it’s a win-win!”

Bruno is also holding on to a few cherished garments from her grandmother that she plans to pass down as well. The first is a clear-bedazzled coin purse that she coveted as a child; the second is a handmade purple and white cotton dress that was passed down to her mother before her. “Three generations in one handmade dress,” she says. “Hopefully I’ll pass it to Mars one day and make it four.”