The Small Business Collection

Stephen Jones x Hiscox

Hats off to the small business owners who do it all

Small business owners do it all, the accounting, marketing, handling of IT issues and the never-ending sales calls. They’re handling a plethora of roles each day and wearing many ‘hats’.

The numbers back this up. Our research* shows that nearly 9 in 10 small business owners regularly take on tasks outside their main role, with many juggling five or more roles a week. From finance and customer service to social media, sales and tech support, it’s a balancing act that’s as relentless as it is impressive.

88% say they feel overwhelmed or out of their depth because of tasks outside their main role. And these additional roles really do add up – small business owners spend an average of 27 hours a week on tasks outside of their core responsibilities.

As a specialist insurer of more than 500,000 UK businesses, Hiscox understands these pressures more than most and we thought it was time that we celebrate the multitasking heroes behind Britain’s small businesses. That’s why Hiscox has teamed up with milliner-to-the-stars Stephen Jones OBE to create a high-fashion hat collection inspired by some of the most common roles small business owners take on.

Running a small business isn’t easy. That’s why the right support is important; so business owners can focus on the things that really matter. Because behind every thriving business is someone spinning a dozen plates and doing it with style.

* May-June 2025 Censuswide survey for Hiscox of business owners with 10 employees or less and sole traders.

Head of Finance

This hat is inspired by tasks such as handling fiddly expenses, tax submissions, foreign currency and invoicing. The hat is money-coloured and the flowers are made from faux £5 notes. The bow takes the form of a giant receipt. In a nod to the stresses of international finance transactions, a second set of flowers show currency symbols from around the world.    

Stephen says: “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.”

Head of IT

Symbolising everything from daily battles with dodgy Wi-Fi through to tackling cyber security threats, the hat features a lifelike recreation of a chunky desktop computer. The ‘screen’ shows a variety of embroidered symbols including the dreaded ‘wheel of death’, while the veil is scattered with keyboard keys.

Stephen says: “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.”

Head of Sales

For small business owners, driving new leads and landing new clients can be an ongoing challenge - one that’s way out of the comfort zone for many founders. Business owners are often juggling networking, website queries and new business calls on top of their core tasks.

This creation brings these realities to life combining, telephones, business cards, and the sales clichés of modern business such as ‘Kerching!’ and ‘Sale’.

Stephen says: “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.”

Behind the designs

Born in Cheshire and educated in Liverpool, Stephen Jones emerged on London’s fashion scene in the late 1970s. While studying at St Martins by day, he was a style icon by night at the Blitz nightclub, known for his unique hat designs.

In 1980, Jones opened his first millinery salon in Covent Garden, quickly becoming the go-to milliner for celebrities and royalty alike, including Boy George and Princess Diana. His hats, often made from radical materials and ranging from refined to whimsical, captured the spirit of the times.

Over four decades, Jones has remained at fashion’s forefront, creating hats for icons like Rihanna, Lady Gaga, and Mick Jagger, and collaborating with legendary designers including Rei Kawakubo, Vivienne Westwood, Thom Browne, and Christian Dior. His imaginative creations continue to set trends, making appearances on runways, in magazines, and at prestigious events worldwide, cementing his legacy as a master of modern millinery.

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