Penelope Chilvers didn't set out to build a global lifestyle and fashion brand. In 2002, she simply wanted to make the perfect equestrian boot, crafted to her own specifications by traditional artisans in the hills of Spain. The result was the Inclement Long Tassel Boot – a favourite of the Princess of Wales, who was first photographed wearing a pair in 2004.
"I didn't have a plan for growth when I started," Penelope tells HELLO!. "I had an art-school training – it grew organically from something very small that then took off. I just ran along with it, keeping up."
© Getty ImagesAnd "never in a hundred years" did she imagine that 20 years later, two of the key members of her team would be her own daughters: Africa works in design and production and Gemma now leads marketing and styling.
In the beginning, Penelope Chilvers was a kitchen-table business, run from home. The designer was a single mother, so the girls were a part of it from day one. "It was all hands on deck," Penelope says. "They were packing boxes, ticking off orders, sticking stickers on parcels."
The siblings were also taken along to trade shows and retail fairs (New York Fashion Week, the Designers & Agents show in New York and Los Angeles), often in the school holidays.
© @wandilton"I had to take them everywhere," Penelope says. The front-of-house selling worked a treat with American buyers. "They loved the little British accents."
For Africa and Gemma, it was a crash course. "It was a baptism of fire," Gemma says, "but you definitely learn selling skills in front of customers, and that sets you up for so many things in life."
Style was always a family conversation – what they liked, what they didn't like, who was wearing what – and vintage shopping together is still a ritual. Portobello Market remains a favourite hunting ground for inspiration, for all three of them.
© @wandiltonCrucially, neither daughter went straight from university into the family business. That was deliberate. "I think we both had a dream that at some point we would join the company," Gemma says. "But it was important for us to find our own way there, rather than going straight in after university."
Gemma trained as a stylist and worked as an assistant to the stylist Elizabeth Saltzman, dressing stars for the red carpet. Penelope hired her as a freelancer to style the brand's lookbooks for years before she joined full-time. Then Covid-19 hit.
"There was no more styling, no more red carpets, no more trips to LA," Gemma says. When a role opened up in the marketing team, the timing was perfect. Today, she oversees brand content, photoshoots, communications, PR and styling.
Africa's route was completely different. She spent seven years as a nursery-school teacher before deciding that she wanted a new career. She joined Penelope Chilvers as an assistant, working her way up and retraining as a designer. She is now part of the footwear design team.
Because she speaks fluent Spanish and Catalan, Africa is able to converse with the family-run factories in Spain where many of the label’s pieces are made. She visits two or three times a season.
© @wandilton"Some of those relationships go back 24 years, to when we started," Penelope says. "It's the second generation now: fathers and sons, mothers and daughters, all working together. The footwear world in Spain is very much like that. It's a small world. We know everybody."
Working alongside her children is a source of deep pride. "It is a rare and wonderful thing to be mothers and daughters working together, and it makes me feel immensely proud as a mother," she says.
But she is also keen to put it in perspective. "We are three in a team of 50 amazing employees with a strong senior team, and we are not a 'family brand' in the sense of its being generational."
The business is run from its London headquarters by managing director Amy Tooley and a senior leadership team. "It's definitely no longer a kitchen table," Penelope says.
© @wandiltonGiven they work so closely together, how do they keep the peace? It turns out that they don’t need to. "People always ask if we butt heads, but we really don't," Gemma says. "We're all aligned on design, styling and marketing, and we understand the brand innately."
Do they find themselves talking shop at family get-togethers? "Yes, or we start talking about it and then have to say: 'OK, let's stop,'" Gemma laughs. "It's so boring for our husbands. They're long-suffering."
Penelope is married to Steve Hastings, while Africa is married to Oliver Travers, with whom she has two children: Noah, three, and Alba, four months. Gemma is mother to one-year-old Moses with her husband, Jake Rogers, who works in tech sales.
The brand’s move into ready-to-wear this spring came directly from customer requests. "We photographed the footwear with clothes, and people were beginning to ask where the clothes were from, [and] if they could buy them," Penelope says.
The collection is vintage-inspired. "I've always worn vintage clothing," she says. Each piece is also designed around the footwear. "There is nothing in the collection that doesn't link to a best-selling piece of footwear, either in the trims or in how you wear them together. It's my safe zone for design.
"We look at all our bestsellers and build clothing around those footwear icons."
For example, the Incredible shearling gilet is based on the brand's popular snow boot of the same name. The piece, which is made in Somerset, has quickly become a bestseller in its own right.
The brand’s loyal customer base extends far beyond the UK. During a 16-day tour of six US states in 2024 – with a heavily pregnant Gemma driving the truck – the family arrived at a stockists’ dinner in Boston to find 30 guests all wearing Penelope Chilvers, some in styles from the very beginning. "It reduced me to tears," Penelope says.
Because the brand’s boots are welted and can be resoled, customers like to proudly show off pairs that they have owned for 20 years. "That's how it should be," Penelope says.
The label also has some long-term royal fans, including the Princess of Wales. "It's wonderful to think that she still enjoys wearing them," says Penelope of Kate’s Inclement boots. "She still has her original pair."
© Getty ImagesAfter the Duchess of Edinburgh visited the brand's stand at the RHS Chelsea Flower Show in May, the team followed her recent trip to Zambia, covered exclusively by HELLO!. During the visit, Sophie wore the brand's espadrilles with a silk blouse and skirt; earlier this summer, she sported the Goldie cowboy boots with the denim skirt from the collection.
"What the royal family do to support British business is something we're so grateful for," Penelope says.
© @wandiltonAre there early signs of another generation of Chilvers creatives in Penelope’s grandchildren? One recently visited the studio and was transfixed by the fabric swatches. Another's favourite activity is putting on his socks and shoes "like a dog holding his lead", his mother jokes.
When asked if childrenswear might be next, Penelope laughs. "No, we are definitely not going into childrenswear." But somehow we feel that Africa and Gemma have other ideas.
