penelope chilvers

Women in Luxury: Penelope Chilvers, footwear designer

03 Sep 2025 | Updated on: 04 Sep 2025 |By Annie Lewis

The English footwear founder pivoted from painting to fashion in 2002 and, happily for stylish women everywhere, never looked back

One assumes there is no pun intended when footwear designer Penelope Chilvers – whose shoes have been worn by royalty (the Princess of Wales, Duchess of Edinburgh and Lady Amelia Windsor) and celebrities such as Rihanna, Alexa Chung and Sienna Miller – says she started her eponymous business on a “shoestring”. Speaking openly about her humble beginnings, Chilvers is now one of the most respected designers in the country, having nurtured and developed her family-run business to become one beloved by women the world over. 

Inspired by the Spanish equestrian aesthetic, Chilvers started designing footwear when she returned from living in Spain with her two daughters, creating a collection of just six boots. Born out of a desire to create shoes that bridge practicality and fashion, Chilvers recalls her shock at returning from Paris Fashion Week in the early 2000s with more orders than she could handle. She soon realised she had something special, but the real turning point came when the then-Kate Middleton wore Chilvers’ Long Tassel Boot in 2006. It put the shoe world in a spin; anyone who was anyone now knew about Penelope Chilvers. With her carefully curated brand in the global fashion spotlight, the following years saw the opening of four London bricks-and-mortar stores, as well as one in the Cotswolds and international expansion into the US market. 

Boots, she admits, are still her best sellers but her brand has since evolved to encompass every lifestyle. Putting as much passion into the finest Goodyear welted ankle boot and the warmest après ski boot as she does easy holiday espadrilles or sophisticated sandals and, more recently, on-trend leather brogues and velvet Mary Janes, Chilvers continues to work with Spanish artisans and responsible factories, whose skills have been passed down through generations to ensure traditional craftsmanship is kept alive.

New for AW25 is the Bloomsbury Collection. Drawing inspiration from the group of London artists and intellectuals who famously lived and loved in Bloomsbury in the early 20th century, the five-piece line leans into androgynous designs that feature intricacies, such as punching, broguing, fringing and buckle detailing, traditionally found in men’s footwear. 

Crafted with the signature Goodyear welt construction – a time honoured construction method that involves placing cork between the sole and insole of the shoe to form a soft, comfortable cushion that moulds to the shape of the foot – Chilvers calls these “hardworking, proper shoes” that are timeless in design and durable in nature, adding: “Look after them properly and you can pass them down to your grandchildren.” 

We sit down with Chilvers to discuss breaking into the industry, working closely with her two daughters, and how she has seen the landscape change for women working in luxury during the past two decades. 

When you were a child, what did you want to be when you grew up?

So many things – I was full of ideas. I remember wanting to be a garden designer. I was up at my grandmother’s in Scotland, she’d give me a tray and I would create a miniature garden within the tray with a mirror as a pond and lots of different moss colours. I’m still not a garden designer but I am a designer.

What was the biggest challenge you faced when starting out in your career?

Cash flow. I didn’t really think it out; it just took off and I wasn’t ready for it. I started on a shoestring with a very small collection which I took to Paris Fashion Week, expecting to take a few orders if I was lucky. I came back on the Eurostar and totted up the number of orders I had taken and wondered how on earth I was ever going to make them because I [didn’t have] a pot of money. It was literally selling to spend again to sell.

Tell me about one of your career highlights.

Most recently, it would be opening our country store. It’s always been a dream of mine to open somewhere out of the city because our brand really embraces the country life. We opened in Stow-on-the-Wold last September and it’s turned out to be a huge success. It’s a very pretty, rural, romantic store.

Did you always have a clear career path in mind and how has reality compared?

I never had a perfectly clear career path in mind but I always knew I wanted to do something creative. When I left art school, I actually thought I might be quite unemployable. In reality, that training opened far more doors than I could ever have imagined. Art school taught me to think differently, to problem solve through creativity, and that skillset has shaped every step of my career.

It led me to a scholarship in Madrid, funded by the Spanish Ministry of Culture, and from there I began my professional journey as a painter, a restorer of historic painted surfaces, and an interior designer. Eventually, those experiences gave me the confidence to establish my footwear business, which I’ve now been running for 23 years. Looking back, I realise that while the path was never linear, creativity has always been the common thread – and it has taken me further than I ever expected.

What does an average day look like for you?

It’s definitely busy! My weeks are built around early starts and, often, early nights. As founder and creative director, I play a large role in the business and lead a big team. We now have five shops across the UK, and my days are full and varied – ranging from back-to-back design meetings to hands-on creative time in the workshop, as well as strategic business planning.

What are the best and worst parts of your job?

The best part of my job is the creativity – being able to design and make things is what I love most, and it’s what gets me up in the morning. The hardest part is the deadlines. In fashion, you have to work so far ahead of the seasons; at the moment I’m designing for AW26 while already thinking about SS27. The timelines are incredibly tight, and the demands of the critical path in the UK fashion industry can be intense.

Both of your daughters now work for your business. Was it important to you to keep it in the family?

My daughters had established their own careers before joining Penelope Chilvers, so I never set out with the intention of making it a family business, but once they came on board, I realised just how important – and rewarding – it is to have them involved. Their contributions have been invaluable in driving our success forward. Gemma leads our marketing, overseeing everything from campaign imagery to social media and PR, while Africa works alongside me in design. They’ve each brought fresh energy and expertise, and I honestly can’t imagine the business without them.

What have been some of the toughest times in your career? What did you learn from them?

Any difficult moment in my career has always been eased by surrounding myself with positive people – they’re my tonic. I try not to dwell on regrets or setbacks, but instead to keep looking forward. When things feel tough, walking is my reset. My home in the Cotswolds, with its garden, is a true sanctuary, and Spain has always been another source of joy and inspiration for me. It’s where I have family, a holiday home, and a deep connection that always reawakens my senses.

I’ve always been drawn to beauty – in nature, in design, and in people – and that love of beauty helps me navigate challenges. More than anything, I believe attitude is everything, which is why I choose to surround myself with positivity and possibility.

How easy do you find it to switch off from work?

I really value family life – it’s the perfect interruption to work, especially now that I have two grandchildren. That said, because I love the creative process so much, I often find inspiration everywhere, whether I’m walking or travelling, so in some ways I never fully switch off. At weekends, you’ll usually find me in the Cotswolds, pottering in the garden, which is a real sanctuary for me. Spain is also an important part of my life and because it’s where our collections are made, I travel back often – for both work and relaxation.

Are you quite strict about taking breaks?

I do check my emails on holiday, but I’m fortunate to have an amazing team who support me while I’m away. I’m not someone who’s glued to my phone, and I’m actually very good at switching off. If I’m heading out for a country walk or wandering down Portobello, I’m perfectly happy to leave my phone at home so I’m not interrupted. I love going off the grid – it feels wonderfully liberating.

What do you do to unwind?

Movement has always been essential for my wellbeing, both physically and mentally. I love being outdoors – whether it’s riding, walking, or gardening – anything that connects me to nature and helps clear my head. For me, it’s not about intense routines but about feeling present, alive, and strong. That sense of energy and clarity always feeds back into how I dress, how I work, and how I carry myself.

Tell me about a woman who has been influential in your career.

My mother has always been a huge influence on me – not just in terms of style, but in the way she approached life with such spontaneity and resourcefulness. Growing up, I saw how she seized the moment with decisiveness. Indecision in my family was overcome by making pros and cons lists. My father would say to us “life is not a rehearsal”: a lesson that has taught me to make things happen in business. I’m sure I’ve made mistakes but I have also learned from my mother to look forward in life. She remains one of my greatest inspirations.

What qualities do you think are most important in a good manager or business leader?

For me, the most important qualities in a good leader are the ability to nurture long-term relationships and to truly value their longevity. Loyalty and trust build over time, and when that foundation is in place, everyone feels they’re working towards the same goal. I also believe fun is essential in a workplace culture – every year we hold a street party in Notting Hill Gate, and it’s something the whole team looks forward to.

What do you think are the biggest hurdles facing women in the workplace now?

Juggling two things that you are passionate about in one day is hard, particularly when half the workplace doesn’t have to go home at a deadline to pick up the children from school. I remember it being really tough but it’s also worth it because children grow up far too fast. You’ve just got to get up and join the five’o’clock club.

How have you seen the landscape change for women working in luxury over the course of your career?

One of the biggest changes I’ve seen, particularly in recent years, has come from the pandemic. Remote working shifted the culture completely, and greater flexibility has now become the norm across the industry. For women, that flexibility has been especially valuable in balancing work and family life. At the same time, I believe it’s important to maintain a strong office culture, so we work to keep a blended week with time together in person for collaboration and creativity.

Bloomsbury Collection penelope chilvers
How do you hope to see it change in the future?

In the future, I’d love to see the luxury industry become even more inclusive, with more women in senior leadership roles and creative positions. Diversity of voices brings fresh ideas, and luxury should always be at the forefront of innovation. I also hope to see a deeper commitment to sustainability and craftsmanship – valuing quality, longevity, and ethical production over short-term trends. For me, true luxury is about creating something that lasts, both in terms of design and the way we build our businesses and teams.

Do you think attitudes to work and careers have changed significantly from when you first joined the workforce?

Yes, particularly since the pandemic. Flexibility has become the norm, and that’s been hugely positive in giving people more control over how they balance work and personal life. It’s allowed many, especially women, to continue ambitious careers while managing family responsibilities in a way that might have been harder before.

That said, I also think there’s something very special about being in the office together. You build a different kind of camaraderie when you spend long hours side by side, and those spontaneous conversations and shared moments are often where the best ideas come from. For me, the blended model works best – it offers the flexibility people value, while still protecting the creativity and human connection that comes from being in the same room.

What advice would you give to young women starting out in the creative industries?

I didn’t really have a plan when I started my business so if you have the opportunity to plan and follow your dreams, I’d recommend that. Always follow your heart because as your work life is so much part of your life for so many years, it’s got to be something that you love.

Visit penelopechilvers.com

Read more: Women in Luxury: Sophie Paterson, interior designer