Simon Leesley and Stitch Fix want to change the way you shop

By combining machine algorithms with personal interactions, Andy Martin dresses down how Stitch Fix’s approach to fashion shopping aims to eliminate ‘the paradox of choice’ while improving your look

Simon Leesley and Stitch Fix UK aim to eliminate the paradox of choice in fashion (Stitch Fix)

Simon Leesley was not always a stylish dresser. He sported cowboy boots while a student at the University of Texas in Austin. Now he has 60-odd “stylists” advising him. I would describe his style as a slim, 40-year-old, laidback CEO look (jeans and jumper), which seems appropriate now that he is head honcho at Stitch Fix UK. The stylists aren’t there to act as his personal wardrobe consultants – they are there for you and me, potentially, to make us look good.

When I went to their HQ round the corner from Holborn station on a cold day in January, it was like walking into summer. They had rails of short-sleeved shirts and skimpy dresses. I found myself ogling a photograph of a gorgeous Dr Zhivago-style overcoat. “The problem,” says Leesley, “is how do you help consumers through all the choices? Most of us don’t have access to a personal stylist.”