What it’s like to run a fashion brand with family

Two sisters walk into a coffee shop carrying the same handbag. “This happens a lot,” Kathryn Allsopp laughs, gesturing between her brown-and-tan Loewe Surplus handbag and the cream version of the same bag slung across her sister Millie Allsopp’s shoulders. By now, they’re used to it — the matching, and the laughter. “Our wardrobes are identical. We turned up to a party the other day in outfits that matched, down to the belt,” Millie says. “We just think the same way.”

As sisters and co-founders of contemporary womenswear brand Usisi Sister, thinking along the same lines can be an asset. “The whole basis of our brand is sisterhood,” Millie says. “I love that we get to work together. It means we share the highs and, of course, the lows — and even with the lows, I have my sister there.”

Fashion businesses have long been family-run — think of the Pradas, the Arnaults, the Guccis, the Versaces and the Laurens, to name a selection. But when designers who aren’t the progeny of fashion dynasties decide to start a brand, the assumption tends to be that they’ll do so with the support of peers, fellow fashion graduates or other members of their chosen creative clans. Not their sibling (unless they’re an Olsen) or their parent. Yet a considerable segment of designers and founders building brands today are finding that they don’t need to look beyond the family tree to find ideal collaborators — and that working with siblings and parents can carry unexpected rewards.

Grace Quinn, sister of designer Richard Quinn and head of sales at his brand, trained as a physiotherapist and never planned to work in fashion. But she was on maternity leave when Richard showed his SS18 collection at London Fashion Week, and he needed support fielding stronger-than-expected sales enquiries. “I thought I’d help out and then go back to work,” Grace recalls.

Then, the next season, the Queen attended his show — her first and only time on the front row — and presented the young designer with the inaugural Queen Elizabeth II Award for Design. Grace never left. Now her presence is invaluable — and the feathered minidress named after her is a perennial hit with partiers and brides alike. “We trust each others’ opinions and instincts,” says Richard, who has dressed Amal Clooney, Princess Beatrice and Sydney Sweeney in his ornate designs. “If she makes any sort of suggestion, I’ll go with it.”

Everyone interviewed here praised the shorthand and innate understanding that a shared upbringing and life-long relationship can bring to working together. “There are no skeletons in the closet when you work with your sister,” says Rosanna Wollenberg. She and her sister Christie left jobs in the luxury sector and branding to launch Otiumberg, the B Corp-certified demi-fine jewellery brand worn by Margot Robbie and Paul Mescal, in 2016. “With a colleague at work, you might not know what’s going on in their life or where they’re coming from. But Christie and I share a lot of values, history and a work ethic. We just intrinsically understand where the other person is coming from 100 per cent of the time.”

Conflict is inevitable, as in any working relationship. With family, it’s quickly metabolised. “You can drive each other nuts, but then you can forgive each other after five minutes and laugh again. And then go crazy again shortly after,” says Charlotte de Geyter, the younger half of the mother-daughter duo behind Bernadette Antwerp, known for modern, bow-bedecked dresses with cross-generational appeal. “My mom has really taught me to stay calm in the face of a challenge, breathe, and then try to solve it.”

“For every problem, there is a solution, no?” says Bernadette de Geyter, Charlotte’s mother and co-founder. “I always say to Charlotte, it’s important that we resolve everything before we go home, because then we can have a good night’s sleep.”

Charlie Casely-Hayford launched the Casely-Hayford brand with his parents, the late Joe Casely-Hayford OBE and Maria Casely-Hayford, in 2009. Following Joe’s death in 2019, Charlie took over design, with Maria as brand director. His sister Alice also works in the industry as a fashion editor.

Charlie views working through disagreement as an essential part of the creative process. “We disagree every day,” he laughs. “If we were on the same page, the work wouldn’t be as dynamic. We’re pushing one another, and that friction, I think, is where the energy and creativity really come into fruition . . . discordant harmony is the goal. That’s where we thrive.”

Not that it’s all conflict — co-working family members describe a number of unanticipated upsides. Business travel can be more pleasant. Cheaper, too. “When we go to Paris for buying appointments, we share a room and stay in our hotel at night, watching sports documentaries,” Rosanna Wollenberg says. “There are no awkward silences, no pressure to go to the bar and get a drink with the boss. It’s just very relaxed.”

Even for sibling co-founders, the Wollenbergs spend an unusual amount of time together. They live side-by-side in near-identical townhouses in Wimbledon, an arrangement that means Christie’s children can jump over their garden wall to reach Aunt Rosanna’s.

Turning off the work-brain can be a challenge, especially when business chat seeps into an out-of-office context. “Sometimes you realise that you’ve been talking about the business maybe to excess,” Christie says. That occurred on a recent trip to Berlin with their father and their middle sister, a yoga teacher. “Our dad was getting very animated, and our sister was getting a bit . . . I wouldn’t say bored, but possibly glazed over. We decided to change the subject and keep drinking wine.”

It can also help make working outside of standard business hours — a given for any small, independent brand — feel like less of a chore. “If we’re working on a Sunday and having fun, it doesn’t always feel like work,” Millie Allsopp says. Holidays together inevitably turn into content-creation trips for their resortwear-centric brand. “Our poor mother is quite often the camera woman,” Kathryn says. (No wonder some founders brand their companies as “family” to encapsulate an all-hands-on-deck ethos, a designation some experts have deemed toxic due to its unrealistic, all-encompassing nature.)

The permeability of family and work life goes both ways. Once, early in his time working with his parents, Charlie Casely-Hayford inadvertently addressed them as Mum and Dad during an external meeting. “It suddenly felt like a parents’ evening. I needed to create some boundaries.” Since then, he’s referred to them as Maria and Joe at work and at home.

The boundaries helped. So did confidence in his own skills and point of view. “I mean, you can’t not touch on the nepo baby thing and imposter syndrome,” he says. “I feel confident in who I am, but also conscious of what you and Dad achieved,” he tells Maria. “That’s probably why I took a different route with the brand, and purposely carved out my own space rather than trying to follow in your exact footsteps.”

Somehow, it works. When asked how much time he and Maria spend together outside of the studio and their Marylebone shop, Charlie answers without pause. “Not enough,” he says. “We do need to spend more time together as a mother and son rather than as business partners. There is a difference.”

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