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

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.”

I am fortunate: I have two sons, both musicians in their twenties, who are infallible sources of wisdom regarding what is in and what is out. My main problem is that they nick all my best gear (I last saw one of my favourite old shirts at the Roundhouse). Stitch Fix offer a more practical “styling service”, relying on a mix of information from you, machine algorithms that sift through the brands, and human consultants who will engage with you on a more personal level, with no notion of pinching your kit.

Simon Leesley’s parents were not that into fashion. His British father was a professor-turned-software entrepreneur and his American mother started a WeWork-type company before WeWork. He did an MBA at Northwestern in Chicago and spent six years with Neiman Marcus working on the financial side at the luxury end of retail. During a stint in management consultancy he ended up working in industrial paints. “That was when I realised that industrial paints didn’t interest me,” he says. Leesley met Katrina Lake, the founder of Stitch Fix, in 2013, and he was “blown away”. A few months later he was launching the men’s and the kids’ lines in the US. He came over to London to head up the UK operation 18 months ago and they launched in May last year.

Stitch Fix aims to tackle what Leesley calls “the paradox of choice”: it’s great, but you can have too much of it. Try looking for a blue dress on Amazon. You’ll be drowning in blue dresses. You need a principle of exclusion. Stitch Fix works like a dating website, except that it’s hooking you up with garments that you will fall in love with. You join up online and fill in a questionnaire about your style preferences, size, and budget, generating 90 data points on average. A package of five items duly arrives at your house for you to try on and buy or send back (normally in a week but extended to 10 days during Covid). Whether you keep or reject, it adds to the store of information about you and finesses the recommendations for the next “fix”.

“Fashion is an emotional category,” says Leesley. The stylists have to be able to develop an “empathetic relationship” with the client, to have a feel for what would suit the customer profile. “The stylist may push the client to be more adventurous,” says Leesley. “Sometimes people say, ‘When I opened the box, I never thought I would wear this. And then my significant other went by and said, Wow’. So it widens the scope. It gives you options.” They have about a 100 different brands on offer, well-known ones like French Connection and Sweaty Betty, and quite a few more esoteric European labels, like Selected Homme, Tiger of Sweden, and Flag & Anthem. They also have their own label, exclusive to Stitch Fix users (Leesley is wearing 01 Algo and Scotch and Soda).

One advantage of the system is that it saves you all that time trooping about and scouring the shops. But is it killing off the high street? Leesley doesn’t think so. “We share information with our vendor partners,” he says. “They see the feedback and it enables them to improve their product offering and sell more in their stores.”

He stresses that Stitch Fix is not a discount outlet. They’re not trying to undercut anyone. Their prices range from £22 for a skirt and £25 for a shirt to around £500. The “style shuffle” option enables you to scroll through different items on the app, as if perusing potential romantic partners. You get to vote thumbs up or down for the latest in fashion. They have now accumulated three billion ratings globally. A fascinating fact: when it comes to denim, the US generally prefers “strait” and “relaxed” (“more room in the thighs”), whereas over here we are “skinny” or “slim” (or even “athletic”). For the time being anyway. The US market is five times bigger than UK, and the clients are bigger too. “Most things here are more tailored,” says Leesley diplomatically.

Apparently Europe and the UK have a big influence on US styles. Trends migrate from here to there. Except where “athleisure” is concerned – all that gym kit (yoga pants, for example) that has come out of the gym and entered the mainstream. But, Simon Leesley assures me the fad for young women in London and Paris to walk around in chunky white trainers with thick soles started right here in Europe.

One of the great mysteries of our time is why we now see guys wearing shorts in the middle of winter. I think this is a fashion that’s gradually crept over here from the States. Maybe it’s something to do with the climate. More likely it’s the fault of the internet: nobody cares what you’re wearing on your legs if your head is glued to a computer all day.