Corporate Couture? Stephen Jones Puts the ‘Many Hats’ of Entrepreneurs on the Runway

If you’ve ever felt like running your own business means being your own accountant, IT support, sales team and cleaner all before lunch, Stephen Jones has just made you feel seen – in couture form. The legendary milliner, who has created show-stopping headpieces for Dior, Marc Jacobs and Rihanna, has partnered with specialist insurer Hiscox to turn Britain’s small business hustle into high fashion.

The project takes the well-worn phrase “wearing many hats” and makes it literal, with Jones creating a series of elaborate headpieces to represent the top roles small business owners juggle each week. Hiscox’s research shows that nearly a quarter of business owners wear five different ‘hats’ weekly, while 88% admit they often feel out of their depth.

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Jones’ creations spotlight three of these roles: Head of IT, Head of Sales and Head of Finance – each a wearable metaphor for the tech, hustle and number-crunching that keep a business alive.

The Head of IT hat captures everything from glitchy Wi-Fi to cyber threats, featuring a lifelike chunky desktop computer on a wide brim, a screen embroidered with the dreaded ‘wheel of death’, and a veil scattered with keyboard keys. “I am under this illusion that I am reasonably good at IT, however when the Wi-Fi goes down, I’m lost. This hat reflects that. It’s detailed, technically complex and engrossing, just like IT can be,” says Jones.

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The Head of Sales is a riot of colour and pop-art energy, with a central red telephone receiver surrounded by floating lips, business cards, and Perspex flags reading ‘Kerching!’, ‘Sale’ and ‘Hi!’. “The hat is fun, lively and all about communication. Because you can have a great idea but unless you sell it, it’s going to stay with you and nobody else,” Jones explains.

Meanwhile, the Head of Finance channels Audrey Hepburn glamour with a white sinamay base, faux £5 note flowers, and a giant receipt bow. “The hat is extravagant, opulent, and confident. It’s not just a fashion statement — it represents the clarity, courage, and boldness you often need when dealing with financial matters,” he says.

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Ed Birth, Head of Brand at Hiscox UK, says the collection “captures the daily juggle that business owners face into and we love how creatively Stephen has brought this reality to life.”

With research showing that small business owners spend an average of 27 hours a week on tasks outside their main role – from IT troubleshooting to social media management – Jones’ hats aren’t just fabulous fashion. They’re a tongue-in-cheek reminder that entrepreneurship is equal parts skill, stamina and style.