Interview: David Lindsay, the Scot behind fashion’s online future

He’s the Scottish digital whizz who revolutionised online shopping with Net-a-Porter. Now David Lindsay is working his magic on the rest of the virtual fashion world

BACK in the olden days, if you wanted to buy a lovely posh frock, a dapper suit or a pair of crazy shoes, you had to go to a shop. This shop (or boutique, as you may well have called it) was almost certainly somewhere distant and inconvenient: London, Stockholm (or, if you lived in the Outer Hebrides, Inverness). Once there, you had to navigate the assistants (usually moonlighting models who made culottes, or mustard, seem like a good idea), find the maxi dress or Crombie coat of your dreams, try it on while the culotte-goddess sucked her teeth outside the cubicle, produce a wad of tenners and then carry it home on the bus.

How our children will laugh when we tell them this story. You went all the way to a building in an out-of-the-way city in the hope that they would have the right item in your size and in any colour but mustard?

And we did. Before we could buy Dries van Noten in our dressing gowns, while waiting for the kettle to boil or for Channel 4 News to start, it was a big old hassle that put off all but the most dedicated. And even when the internet started, the received wisdom was that people would use it to buy books and CDs, groceries and concert tickets. Five-figure frocks, the ‘experts’ reckoned, needed a Bond Street address, a sales assistant to bring modom the matching handbag, a velvet-curtained changing room and a full-length mirror for pre-purchase twirling.

While shoppers were still looking at Vogue and GQ’s tiny-print stockist listings and bursting into tears, David Lindsay had left Edinburgh armed with a degree in electrical and electronic engineering. In London, at the turn of the century, during the first wave of the dotcom boom, he spent four years on football websites. This might sound like a testosterone-meets-technology dream scenario. Lindsay, however, is not like that. He is that rarest of creatures, a geek who loves shoes.

Even so, his first encounter with Net-a-Porter, in its early days of selling elite fashion online, did not go well. He continued shoe shopping and creating drop-down menus of midfielders. When he eventually met the site’s visionary founder, Natalie Massenet, it all fell into place. “We got on really well,” he recalls. “A shared love of white space and Apple products. It was a natural fit from then on.

“I think it was the industry I was born for. My favourite things, except for family and my miniature dachshund, are shoes and technology – and shopping for both. I get the same little soul uplift from my copper Florsheim by Duckie Brown brogues as I do from my iPhone.”

Massenet immediately identified the factor that has made Lindsay the go-to guy for your high-fashion website. (His post-Net-a-Porter CV reads like Carine Roitfeld’s shopping list.) “Natalie used to make fun of me,” he recalls. “She reckoned I thought like a girl, and that may be true. I knew about retail and I knew how I wanted to shop for fashion.”

His days at the company (he left in 2009) were not spent in the stock room among the Missoni trainers. Lindsay describes himself as the swan’s feet, paddling furiously under the surface while the website unrolls at the command of the mouse, seamlessly tempting the customer in, guiding them towards the perfect Stella McCartney jacket or Acne jeans and delivering it wrapped like a gift the next day. “Together with the developers, we built a system to try to control every aspect of the business, with centralised product and customer databases so that everybody in the company acted on the same data.”

This doesn’t sound terribly fabulous, admittedly, but it does sound like common sense. Yet it was fighting talk in 2004. “I understood what Natalie was trying to achieve and made sure we were able to execute it: I had a vision of how that should work and I was probably pretty bullish in forcing it into the organisation.”

It was this overview, the codes and algorithms, that made the shopping experience so utterly seductive, that broke the mould of internet shopping and proved millions would spend thousands of pounds on designer shoes and cocktail rings at the click of a mouse. “I think Net-a-Porter was secretly a luxury logistics company. The systems we built allowed us to do things our competitors couldn’t: same-day delivery to London with liveried vans and drivers; international pricing engines that allowed the brands to control their pricing.

“These were the real game-changers. They helped raise the luxury bar to a level that was impossible for potential competitors to attain easily. Also, the customers loved it.”

Since leaving Net-a-Porter to join the international marketing agency Wednesday, Lindsay has gone on to work with just about every other fashion brand with an impressive online presence. “It still surprises me just how much respect and clout the name carries. People are always telling me that their new project is going to be the Net-a-Porter of something or other. The weirdest was ‘the Net-a-Porter of pet supplies’. That was a relatively brief conversation.”

One of the things he enjoys about working with Wednesday is the range of clients: Balenciaga, Alexander McQueen, Proenza Schouler and Liberty, as well as Aldo and H&M. What they want has gone way beyond the website. “Almost every brand wants to talk about mobile content, cross-channel initiatives and social media. Responsive design [where the site changes depending on whether it’s being viewed on a phone, tablet or big screen] is another biggie. Even in the past couple of years, I’ve seen a step-change in the amount of attention, focus and money brands are prepared to push at their digital initiatives. For me, the dream scenario is a business with an open mind but not necessarily a fat wallet.”

The future will, he thinks, only get more exciting. One stumbling block at Net-a-Porter was his refusal to believe a computer could not pick out the perfect shoes to go with a dress. “I’ve got the sort of confidence in technology that means I can’t see a problem without trying to architect a technical solution. Online fashion didn’t, at first, seem like it should be any different.”

He was going to programme a computer to style an outfit, so that when a customer looked at, say, a Hervé Léger bandage dress, they see it teamed with Erickson Beamon earrings, a Pamela Love ring, Givenchy shoes and a Bottega Veneta bag. It would also generate the thoughtful suggestions at the side of the page: more Léger, other brands that make similarly unforgiving frocks and, more realistically, Spanx. “I wanted to build an algorithm that could satisfy a fashion Turing Test, so an outfit created by a computer would be indistinguishable from one created by a stylist.” (Alan Turing tested computers by assessing whether their speech could be distinguished from a human’s.)

It took him over a year to admit it wasn’t happening. “We can make computers do things that humans cannot, like analysing huge amounts of data, but we struggle to get them to make subjective decisions. We never got very far with automating what the outfitters seemed to be able to do innately.” The bag that works so well with the dress, or the scarf and jeans that work so well with the shirt, like every other putative outfit on Net-a-Porter, is selected by a human.

What Lindsay failed to anticipate, however, is that social networking is now doing the job for him. “Facebook, Twitter, Pinterest, You Tube, Polyvore and the fashion blogging network have brought about a beautiful mass democratisation of that function. Clothes and shoes now have a their own social content life, separate from the originating sites. The challenge is to aid and ease consumer access to that content. “I see it as a kind of global fashion-consciousness; the next generation of tools and search engines will be able to tap into that consciousness, giving consumers the ability to play with that content.”

In the future, when you google the Leger bandage number, not only will you see Net-a-Porter’s suggestions of what ring to wear with it, but how other stores have styled it, outfits Polyvore users have put together with it, fashion bloggers’ considered opinions, paparazzi snaps of celebrities wearing it ... It is not inconceivable that it could have its own Twitter feed and friends on Facebook. “The job of the brands and stores is to feed this global fashion-consciousness with high-quality images, content and product.”

And make it much easier for us to buy even the most sublimely impractical, uncomfortable and fabulous garments known to man while wearing our joggers.