Milliner-to-the-stars Stephen Jones partners with Hiscox to create a whimsical range of 'corporate' headpieces, illustrating the 'many hats' Britain's small business owners wear on a daily basis

News provided by

Hiscox Group

31 Jul, 2025, 06:00 GMT

HATS OFF (OR RATHER ON) TO SMALL BUSINESS OWNERS

  • New data from Hiscox reveals how small business owners wear as many as five different 'hats' in a normal working week, with three of these represented in showstopping fashion via headpieces created by esteemed milliner Stephen Jones
  • The 'Head of IT' hat features a recreation of a giant desk top computer, the 'Head of Sales' hat focuses on a red telephone handset, while the 'Head of Finance' hat incorporates a stunning receipt bow and faux £5 note flowers
  • To view the hats, visit Hiscox.co.uk/hats

LONDON, July 31, 2025 /PRNewswire/ -- The colourful (and at times chaotic) world of small business life has been stylishly immortalised in a series of playful, high fashion hats, created by legendary milliner Stephen Jones; the man behind head-turning designs for the likes of Dior, Jean Paul Gaultier and Marc Jacobs.

Commissioned by specialist insurer Hiscox, the high king of headwear took a break from designing for global fashion houses and A-listers to focus on hardworking small business owners, who spend their time juggling a host of different roles, or wearing 'many hats', to keep their businesses ticking over.

Three of the most common 'hats' they don are Head of IT, Head of Sales and Head of Finance, and it is these three business-integral positions that have been brought to life, in quite a literal sense, as show-stopping headpieces.

About the hats

  • The Head of IT hat captures everything from dodgy Wi-Fi battles to serious cyber threats. Its wide, square brim frames a chunky desktop computer replica, with a 'screen' embroidered with a spinning wheel of death and a loading message. Keyboard keys dot the veil, and a computer mouse doubles as a dramatic hat pin
  • The Head of Sales hat is a bold, pop-art celebration of communication. A bright red phone receiver takes centre stage, surrounded by floating lips, business cards, and Perspex flags emblazoned with sales clichés like 'Kerching!', 'Sale', and 'Hi!'
  • The Head of Finance hat is a delicate elegant creation that is the colour of money. Inspired by Audrey Hepburn's My Fair Lady headpiece its white sinamay base is adorned with feathers, faux £5 notes flowers, and decorative flowers showing currency symbols

About the research

While the hats scream haute couture, high fashion and unrestrained blue sky thinking, their creation is inspired by data. New research from Hiscox to accompany the hats' release shows that almost a quarter (23%) of small business owners* wear as many as five hats a week, and 88% say they feel overwhelmed or out of their depth because of tasks outside their main role. 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.

A deeper dive into the data shows that over one fifth (22%) admit to struggling with IT issues, and 20% say they find legal and compliance issues tricky to navigate. A similar proportion (20%) say the thing they find most challenging is avoiding burnout and mental health strain. When faced with challenges outside of their comfort zones, it's not surprising that 25% confess to turning to YouTube tutorials to brush up on skills outside their wheelhouse.

Commenting on his dazzling small business owner-headwear creations, Stephen Jones said: "As a milliner and small business owner, I wear many hats in business, but it's the metaphorical ones that are the hardest to pull off. You're expected to be a finance expert, IT whizz, and salesman to name but a few, and this project is a love letter to the small business owners doing it all themselves. The hats bring those everyday roles to life in unexpected ways that are full of flair, humour and a bit of fabulous chaos. They're energetic, and charming like the small business owners they represent."

Ed Birth, Head of Brand at Hiscox UK, added: "We know small businesses, and we know that running one can be exciting, exhilarating, unpredictable and at times overwhelming. It's a steep learning curve and a balancing act that most handle exceptionally well. This collection captures the daily juggle that business owners face into and we love how creatively Stephen has brought this reality to life."

The top list of hats worn by small business owners is as follows:

  • Head of Finance
  • Customer service lead
  • Admin and office manager
  • Head of Sales
  • Social Media Manager
  • Marketing Manager
  • Planning Director
  • Head of Design
  • Cleaner
  • Head of IT 

To view Stephen Jones' creations for Hiscox, please visit www.hiscox.co.uk/hats.

NOTES TO EDITORS

*All statistics quoted have been taken from consumer research carried out by Censuswide for Hiscox between 25.05.25 and 04.06.25. 500 small business owners in the UK were surveyed and for the purposes of this research, small business owners have been categorised as businesses with 10 employees or less and sole traders.

Photo: https://mma.prnewswire.com/media/2741110/Hiscox_Group.jpg