How artificial intelligence hacked men’s wardrobes

Retailers are increasingly using algorithms and customer data to tailor our shopping experience online. Is this the death of personal style?

Once upon a time, there was a place called the High Street. Here you’d find a butcher, a baker, and a gentleman’s outfitter, where the chap behind the counter was most likely the manager, owner and buyer. He knew if you needed a new suit for work or a jumper for the weekend. In fact, he probably sold you your last one. ‘Each shop had its own take and a very personal relationship with local customers,’ says the celebrated tailor, designer and retailer Timothy Everest MBE, who began his career at Tommy Nutter.

In London, independent boutiques such as Hideout, Jones, Browns, Zee & Co and Woodhouse offered the latest fashions to men based on this local, intimate model: Zee & Co was for the suburban garage geezer living it large on the weekend; Browns and Jones your high-fashion hairdresser, Hideout was the original importer of US street and skate wear. For decades, this was how men shopped for clothes in Britain.

In the 80s and 90s, huge designer flagship stores, shopping centres, fast fashion and the arrival of department stores with big, multi-brand menswear departments replaced the intimacy of independents with theatre and showmanship. The designer flagship was primarily an invention of brands like Armani and Ralph Lauren. They were fantasy worlds unto themselves.

Some of the original independent boutiques, such as Oi Polloi from Manchester or Matches from Wimbledon, morphed into online destinations in their own right. In 2017, was sold to the private equity firm Apax Partners in a deal that valued the company at $1billion. In 2015, Browns was bought by Farfetch for an undisclosed amount. Many more have been consigned to retail history. James Jebbia, the founder of Supreme, cited the Duffer of St George as one of the pioneers of brand collaborations and a key influence on his billion dollar streetwear company.

‘Everything we do has to be backed up by data’

Shops, quite simply, were where menswear happened. ‘I was speaking to the founder of Matches, Tom [Chapman], the other day, and he said that they never dreamed online would overtake sales on the physical premises,’ says Everest. ‘Or that people would spend that kind of money on big-ticket items online.’

So what is the alchemy by which this process happened? Today, shopping for clothes has become turbo-charged by technology, and in the process, fashion has become something of a science.

Erik Stjernstrom, Head of E-commerce at London tailoring and accessories brand Drake’s, which operates both bricks-and-mortar retail locations and an e-commerce platform, says: ‘The big change is that we’ve gone from an industry that relied on pure gut instinct to one where everything we do has to be backed up by data.’

Algorithms, powered by customer data, are the secret formulas that imperceptibly influence what we see and buy. They have just as much power over what we wear as a fashion editor or an influencer. They’re used by companies like Drake’s and e-tailers such as Mr Porter, Matches and Browns to inform buying and design decisions.

‘Everything we do at Drake’s is about personalising the experience for customers,’ says Stjernstrom. ‘The data allows us to segment our customer at an increasingly granular level, which helps us find out how we can best serve them.’

This could be very obvious, like not showing customers in Australia sweaters during summer. Or localised merchandising that differs from territory to territory  (Scandinavians, true to type, prefer more minimal and simple products). Some of the most valuable data will be that of the VIP customer who drops more than £20k per year. This information will be used to encourage them to buy even more, and to attract more big spenders to the brand.

The digitised world also informs the ways in which clothes are designed. Products from the private label brands of e-comm sites like Mr Porter at the luxury end, and Amazon for the mass market, are designed by learning from the platform’s bestselling products. Let’s say an online e-comm platform wanted to make a bestselling white button-down shirt. The design team will examine the top 20 bestsellers for fit, fabric, detail, price, quality, and also data that tells them which shirts were returned and why. Was the collar a little too high? Were the buttons too thick? Distil all that down, and et voila.

If that all sounds a bit like something out of Black Mirror – don’t worry. The brave new world of technologically enhanced fashion still needs input from humans. Online platform uses a questionnaire to figure out what type of man you are stylistically: streetwear hypebeast or nouveau mod? Scandi minimalist or flamboyant dandy? Its algorithms will then offer you a selection of clothes based on these menswear archetypes. ‘The algorithm on its own can’t figure everything out,’ says Tim Grimsditch, Thread’s Chief Marketing Officer. ‘It’s only as good as the human input.’

Originally, Thread assigned humans to customers to make recommendations, just as a shop of the past would have, but as the company grew, that became unsustainable. Today, a team of stylists map out evolving menswear tribes using old-fashioned IRL observations, after all, fashion takes place on the street, in clubs, restaurants, magazines and at fashion shows. Then these stylists work with programmers to refine the algorithm so that the recommendations keep up with what’s going on. ‘In the old days, dress codes were more defined,’ says Grimsditch. ‘You wore a suit to work and jeans at the weekend. Today, not only is that much more fluid, but also, men need help to choose from the increasing amount of product that’s available.’

‘The algorithm on its own can’t figure everything out. It’s only as good as the human input’

Technology has also led to the ‘financialisation’ of fashion, especially in the secondary markets for collectible streetwear. Platforms like StockX and Grailed act like financial markets, only instead of stocks and shares, they trade grail-worthy trainers and streetwear. Resellers now write programs (‘sneakerbots’) that will automatically buy the latest Yeezys within seconds of them going online, in order to flip them at a profit on these platforms. ‘There’s more money to be made from a box of trainers than there is from a bag of weed,’ says Ryan Barr, co-founder of The Drop Date, a trainer news site that reports on the latest releases. ‘Kids are buying sneakers to flex just once on Insta before flipping them at a vast profit.’

What does the future hold? Kathryn Bishop, Deputy Foresight Editor at The Future Laboratory, one of the world’s most renowned futures consultancies, says: ‘There’s a huge amount of waste in the fashion industry. The latest research shows that Brits waste £83 billion on clothes we don’t wear. There’s a great opportunity to use this technology and data to create a more sustainable fashion industry.’

She cites platforms like Save Your Wardrobe, which allows users to upload the contents of their wardrobe online, so that you only buy what you really need. Others such as Finery allow users to upload up to 10 years’ worth of receipts in order to chart your style progression.

Drake’s is currently working on tech that will help them visualise made-to-measure tailoring online. ‘We’re going to think back on the days when you only saw clothes online in two-dimensions as odd,’ says Stjernstrom. ‘The dream is that once you’ve been measured by a person in one of our stores for a suit, you’ll be able to go online and order more wherever you are.’

Everest recently launched his latest ‘bespoke casual’ retail concept with premises on Commercial Street and Fashion Street in Spitalfields. Here, made-to-measure casual clothes and tailoring are visualised on an iPad, so that the customer can make modifications to linings, widths of lapels and top stitching, in conjunction with a stylist. ‘It means they’re involved in the design process,’ says Everest.

Some worry about filter bubbles taking the spontaneity and joy out of shopping, and that style won’t progress or evolve if left to an algorithm. Everest, who has dressed everyone from Mick Jagger to David Bowie, thinks differently. ‘In many ways, all of this technology is an evolution of what we’ve always done; helping the customer find their style. And at the end of the day, the only way to be modern is to be yourself.’