Businesswoman, female founder and creative, Penelope Chilvers values family, beauty, travel, and connection to keep her centred while running her eponymous footwear brand. Launched 23 years ago after showing a small capsule collection of beautifully crafted Spanish riding boots during Paris Fashion Week – taking orders from stores around the world on the back of an envelope – the brand now has a glittering fan base, including the Princess of Wales, Rihanna, Cate Blanchett, and Sienna Miller.
At the heart of the family-run brand lies craftsmanship, integrity, and sustainability, imbued across the Penelope Chilvers collection, which encompasses everything from boots, espadrilles, and Mary Janes to bags and belts. This season, the designer also debuts a neat and chic Penelope Chilvers clothing collection called Chapter 2. When not working, walking, riding, or travelling, Penelope finds comfort in snuggling with her young grandchildren and exploring the world in search of inspiration. Here she tells us how she stays calm and grounded.
Penelope Chilvers wearing her Goldie Cowboy Boots (left), and hand selecting leathers in Spain (right)
What inspired you to go into making shoes and boots?
It hasn’t been a conventional journey – I began my career as a painter then later moved into designing interiors and fashion. I was always drawn to the tactility of things handmade, to colour and heritage, and to stories woven through craft, but it was while living in Barcelona, riding regularly in the Collserola Park with a friend, that led me to commissioning the perfect pair of riding boots from a talented artisan whose clients had included famous bullfighters and Hollywood film stars in the Seventies.
How did that kickstart your brand?
They were my dream boots, made to my measurements, and on return to London, all my friends wanted to order some. It kickstarted me into designing a capsule collection of six equestrian-inspired boot styles with the same Spanish maker, which led to opening my first shop in 2004 in Notting Hill as a destination for women looking for beautifully crafted, timeless footwear with a strong sense of individuality and provenance.
How has your creativity helped build your brand?
It means I generally have a positive attitude to life and find things normally work out better than expected – but this isn’t to say I don’t doubt myself. Talking things through with my husband always helps to restore faith in myself.
What gets you out of bed in the morning?
What began at my kitchen table when my daughters Gemma and Africa were little, now 32 and 35, has grown into a business I’m deeply proud of, and they’re now both invaluable members of the team. I also feel a strong sense of responsibility to my team – watching people within the business thrive, grow, and flourish is one of the most rewarding parts of running my own business. It never feels like ‘just a job' – it feels like a privilege.
Penelope with her daughter, Africa on the riding safari with Ride Botswana (left); Penelope with both daughters, Gemma and Africa, outside the Penelope Chilvers Country store in Stow-on-the-Wold, in the Cotswolds (right)
How does working with multiple generations inspire your work?
The team ranges in age from early twenties to sixties – a true reflection of a footwear brand that speaks to women of all ages. My daughters keep me young with their energy and fresh perspective, ensuring the business stays relevant in an ever-changing world, whilst remaining true to what we believe in. We collaborate with trailblazing women, like India Hicks and Alexandra Tolstoy. It’s important to stay curious, adaptable, and authentic.
What lessons have you learnt from the footwear business?
Footwear isn’t an easy craft. It’s complex, precise, and time-consuming – learning directly from artisans who’ve honed their craft over generations has taught me the value of strong, long-term relationships built on trust, patience, and mutual respect. Their unerring dedication and skill have taught me everything I know.
And when it all goes wrong?
My tonic is to surround myself with positive people and to try not to dwell on regrets. Disappearing into my Cotswolds garden is my way to reset. As I wander through the paths – deadheading blooms, pulling weeds, breathing in the green freshness – I feel my senses awaken again.
What makes your house feel like 'home'?
Home is where everything comes together, and the kitchen is very much at the heart of that. I recently designed my dream country kitchen with Neptune – it’s intimate, cosy, and perfectly suited to our farmhouse. I designed it as a space where we can create countless family memories for decades to come, especially with little details like cabinets hand-painted with butterflies that the grandchildren will remember.
Penelope in her Neptune kitchen, wearing her Watercolor Stripe Trousers and Flora Velvet Espadrilles (left), and her hand-painted butterfly cabinets (right)
What things at home make you happy?
I love collecting textiles, many of which inspire my work in the studio. For example, I invested in some curtains made in a beautiful brown striped merino wool designed by Tori Murphy who I met years ago at the Chelsea Flower Show – they not only remind me of traditional Spanish donkey blankets, but I like surrounding myself with pieces made by people I know because they hold greater meaning while connecting back to craft and tradition which is what makes my home feel truly special.
Where do you find sanctuary in your day?
My Cotswolds workspace is where I surround myself with favourite textiles, objects, and memories that spark new ideas. Having that balance between a lively, open home and a private escape for reflection gives me both comfort and energy.
How do you find peace of mind?
Walking is my daily ritual. Whether I’m in London or the Cotswolds, I make time to walk every day. It’s when I think, plan, and reset, while also fitting in some exercise. When I’m working in Spain, I always stay a little distance from the factory so I can walk there and back each day. It’s why I added walking boots to our collection – walking connects us to ourselves and our surroundings in a way that boosts our creativity.
And when you’re not working…
I’ve always travelled with my daughters, often back and forth to Spain, but now they are older, our journeys take us further afield. Last January, we collaborated on Safari riding boots with Ride Botswana – to be able to experience riding through the raw beauty of Africa was extraordinary – and a few years ago, we partnered with Suján safari camps in India to support a Rajasthan rewilding project. It’s rewarding to be able to use my business as a platform for exploring the last wildernesses of the world, finding inspiration in them, and then giving something back to protect them.
Penelope in her Cotswolds garden (left); and with her family (right)
What about your skincare and self-care routine?
I’m a big fan of Trinny London skincare and make-up, which I use every day. For me, self-care is also about movement and stillness in equal measure. I practice yoga regularly to support both my body and mind, giving me space to breathe, reset, and find balance.
What does 'luxury' mean to you?
Time is the true luxury: time to be generous, time to share kindness, and time to laugh. It’s also in the simple things – making a delicious soup, drinking a glass of good wine with my husband by the fire, or enjoying cuddles with my grandchildren (being ‘Iaia’ – Spanish for granny) has brought me such unexpected joy.
What can’t you live without?
I try to find joy in the small things: a magnificent sunrise, an intimate conversation, a drive in my car with the radio on loud. But for naughty indulgences, I can’t say no to Mochi ice cream or toasted sourdough slathered with Marmite.
If you could give your younger self one piece of advice, what would it be?
Don’t let fear hold you back. Be brave, take the leap. It’s always worth trying. Some of the most important moments in my life and career came from trusting my instinct and stepping into the unknown. A quote by the Spanish poet Antonio Machado – ‘Traveler, there is no road; you make your own path as you walk’ – has become something of a quiet mantra for me and a reminder that life isn’t mapped out. You create your own journey one step at a time.
Shop the Pieces That Contribute to Penelope's Daily Rituals
Penelope had curtains made in this Tori Murphy fabric and favors the brand for its 'connection to craft and tradition'. The sumptuous merino wool brings understated luxury.
Trinny London is Penelope's makeup go-to and this sheer shimmer balm in Violine is her favorite shade for a natural glow.
Penelope says walking is a daily ritual for her, which is why she added walking boots to her collection. These classic boots in waterproof oiled suede are durable enough for everyday without sacrificing on style.
Enjoying a good glass of wine by the fire with her husband helps Penelope unwind at the end of a busy day, and these colored stemless tumblers are a similar style to the ones in her kitchen cabinet.
These suede cowboy boots are an absolute Penelope Chilvers classic. Ready to pull on and dress up with a floaty floral dress or pair with jeans for dressing down.
If you have a lot of shoes and boots, like Penelope, investing in some large storage baskets like this to keep under a bench near the front door will help to keep your entryway clutter-free.
This interview is part of the My Ritual series from Homes & Gardens, which explores the ways that leading tastemakers find calm and connection in their busy lives. Part of our wellbeing and sanctuary content, you'll find plenty of tips and nuggets of wisdom as well as product recommendations to help you create your own daily wellness rituals, for a healthy body and calm mind.
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