I Let AI Choose My Outfits for a Week. Here's What It Did to Me

The algorithm is coming for your clothes, with the launch of data-led subscription box services. But do they really make you look good?
Ryan Bassil
London, GB
AI clothing box
Background image taken from THREAD, Stitch Fix and Outfittery websites

Like gourmet food, books, vinyl, whisky, watches, coffee and sex toys, you can now have men’s clothing shipped to your door in a subscription box. Specifically, that entails the arrival of a huge cardboard box packed tight with seasonal essentials. This isn't a standard clothing delivery, where you've scrolled endlessly through an online store sale section, then inevitably ended up getting a new, un-discounted drop saved in your 'favourites' at 1.37AM the night before. Instead they're selected, depending on the service you choose, by data scientists, AI and teams of keen stylists.


Think of these boxes as the next base in fashion’s tech affair. Facebook is developing AI technology, called Fashion +++, to elevate your look; meanwhile, last month, Amazon launched their AI app Style Snap (basically Shazam for clothes). Clearly, the omnipresent, multitudinous ‘algorithm’ is not content with monogamy. After solidifying relationships with music, film, TV and your newsfeed, it’s about to fuck with your style.

You could say that these clothing boxes are marketed at the same sorts of people who commit to assembling Hello Fresh recipes past the free trial period. In that way, the boxes aim to provide high quality garms for men who either don’t have time to shop, need a stylist, or both. But do they work?

I signed up to three services. First, THREAD, an artificial intelligence start-up that received a $13 million investment from H&M’s venture arm CO:LAB last year. Then Stitch Fix, that, along with picks from stylists, runs suggestions via an algorithm created by their 100+ data scientists. And, lastly, Outfittery, which also uses a combination of artificial and human intelligence to select their clothes.

So, how does it work?

Each service requires you to fill in a questionnaire. Those vary slightly from brand to brand – Outfittery asks if you’re looking for stuff for a specific occasion, like a wedding or night out; Stitch Fix wants to know how you commute to work – but they all cover the essentials: weight, height, fit.

You’re also asked a few broader style questions. Stitch Fix and Thread both provide images of various fits – you tell the service whether you’re into them or not and this feeds into the algorithm. The same goes for brand choice. Stitch Fix and Outfittery both fling various logos in your direction (All Saints, Fred Perry, Reebok, etc) to see what you'd want to hold onto. A few bits of detail later and you’re all set. The data gets fed into the algorithm and the service designates you a stylist.


THREAD is the most detailed of the three – I'm immediately assigned to a lad called Luke, who pops up in my email inbox with a note and headshot so I can see who he is. He tells me he's "written and edited an online menswear journal for the past two years", though doesn't specify which one. The message is also automated, making it feel less human and like a creepy insight into our AI future.

Stitch Fix keeps things low-key. No boys jump into your DMs. Instead you're told who your stylist is in a note accompanying your clothing delivery. In my case, I'd been styled by a woman named Katie – though without personal details and an image, it wasn't clear "who" she was. Meanwhile, Outfittery, the most human of the lot, include verbal interaction in their service. AKA, the stylist calls you up to go through some style stuff – though this is mostly about you and what you want, than their previous work.

Finally, the items go in the post. Voila!

So, what does it look like?

A bit about me: I’m 27, rarely if ever do I dress in anything smart; I like wearing colours, like in the photo above (I'm in green jeans). On an average Monday, though, I want my fit to feel as close to being in bed as possible. I fed a version of this information into each program, asking Stitch Fix and THREAD for a casual look, as well as adding ‘day-to-work’ wear into Outfittery for some variety.

First up, THREAD. They differ slightly from the other two brands by emailing across a full outfit in advance; you then choose whether to buy or leave it, whereas the other two services don't let you in on what you've ordered until it arrives (though you can send unwanted items back, and only pay for what you keep). My (robot? real?) boy Luke from THREAD had suggested a casual, dressed down lewk.

THREAD clothing

A casual fit from THREAD

Not my usual bag, I’ll be honest? The blue and black in the same fit threw me. Though several men still commit this mistake, it’s common knowledge these colours simply do not go well together. A quick Google also showed the pair of shoes they’d offered (Cole Leather Trainer from Shoe The Bear) was available from other retailers for £29 less than they cost through THREAD.

Next up: Stitch Fix. Consider them a bit of a Silicon Valley rarity because unlike Spotify, Slack, Netflix, etc, they actually turn a profit. Valued at $2.3 billion, they launched their UK arm earlier this year. Vogue.co.uk have also interviewed their founder. I was excited.

Stitch Fix clothing

A look and another look from Stitch Fix; jeans, model's own


Three more Stitch Fix looks

I’d completed the 80 questions in Stitch Fix's style survey, pre-fix, and thought the algorithm knew me well. But… wuh-oh! Maybe not. Of the items I received – All Saints jumper, Lyle and Scott t-shirt, orange shirt, pink jumper and a blue one, from one of Stitch Fix’s own brands (both they and THREAD sell in-house items alongside high street names) – just one, the leopard print All Saints jumper, fit my style.

A spokesperson says the service gets better with use. ie: you note the items you don’t like and why in Stitch Fix’s check-out review, then return them free of charge, then book in another fix. With each go, the data you provide helps the algorithm select better items – which the stylist then combines into a look.

Round number three: Outfittery, the highest end of all the boxes on offer.


Oi, oi – pass the stocks! A fit by Outfittery

Outfittery clothing

Three more fits, by Outfittery

The most muted of the three services, Outfittery looks to be designed with the big boy business man in mind. Just check me out up top in a suit! Due to the phone call and variety of items on offer – two full looks: one for “work”, if I went to that kind of formal-looking “work"; one for a relaxing weekend – it’s also the closest of these services to a full styling experience. In a high-flying life, maybe I’d wear this stuff.

Dressing yourself is an inherently human experience. We decide not to be naked. We choose what clothes we’d like to wear each morning, having already picked them from the shop. So, bringing technology into the picture feels clinical. If you’re into fashion, you appreciate small quirks. Like the way someone’s fit pops, thanks to a splash of colour on their socks. Or a one-off find: whether it’s a hand-me-down, charity shop choice or high-end sweatshirt available in a limited run.

These services currently do little to satiate this thirst. They, essentially, offer outfits set to a specific archetype – guy who likes to wear comfy sportswear on the weekend; dude who thinks wearing faded pink is adventurous; dull tones, upon dull tones, upon dull tones. Blue, black, grey and green.

Spotify’s algorithm helped generate a genre of music. Spotify-core, or streambait pop as Liz Pelly defined it in The Baffler , “is a type of music that could easily fit on mood-and affect-oriented playlists like ‘Chill Hits’, ‘Chill Tracks’, or “Sad Songs.’”. Right now, AI powered styling is, in effect, the same thing. It’s not pushing the boat out. It’s dressing men how they’ve always dressed.

For some men, putting on the same three looks as everyone else is OK. They arrive home late, daily, with little time for anything else but a pre-prepared meal and two episodes of Netflix. They read the news they’re given. Perhaps they would like clothes delivered on a monthly or seasonal basis, without the stress of picking them out. Perhaps it’ll free up their time for more work.

Removing the hours spent looking for clothes is the “advantage” of these services. Will they make you stylish? Depends how you define looking good. Crucially however, they cultivate a lifestyle where you can return to these boxes again, and again, to feed the big data algorithm. Luxury capitalism, now!