Amazon judges your style, so we judged it

It's camera-equipped Echo Look uses AI to evaluate which outfits look best on you

Lately I’ve been putting on my pants in front of a camera. Dressed, I say out loud, “Alexa, take a picture,” and Amazon’s tube-shaped Echo Look snaps a shot. Moments later, a photo of me modeling the day’s clothes appears on my phone. If I change outfits and ask Alexa to snap again, the $200 camera goes further: It judges which ensemble looks better.

Yes, judges—as in, what were you thinking wearing those white skinny jeans? Amazon has used technology as a tastemaker since it began recommending books in the late ’90s. But how could a machine possibly weigh something as complex and subjective as personal style?

To find out, I called the human fashion police: Hal Rubenstein, a founding editor of InStyle magazine, Teri Agins, longtime Wall Street Journal fashion columnist, and stylists Paul Julch and Solange Khavkine.

My colleague Joanna Stern and I played dress-up with nearly two dozen outfits, comparing the Echo Look’s robo-judgments with those of the experts. Here’s the thing: The machine was surprisingly on point in most head-to-head comparisons. But even if computers can master current trends, they still can’t replace that friend who takes you to the store and says yes, go for the floral-print bomber jacket.

Amazon isn’t disclosing how this Style Check feature makes decisions, saying only that humans help the AI algorithms “get smarter over time.” The Echo Look, which also does everything Amazon’s other talking speakers can do, is for now sold only via invitation.

It takes a big leap to install an internet-connected camera and microphone where you usually disrobe. Unlike Amazon’s similarly named Echo Show, the Echo Look isn’t always on. It takes a shot when you verbally command it, and there’s a button that shuts its sensors off. Amazon stores the photos for your reference—and so it can keep learning. Who would even desire such a thing? If you love fashion, the Echo Look could be a handy tool to capture, collect and rank outfits. For the rest of us, at best it offers low-anxiety second opinions.

The idea of a style robot “is hilarious, ludicrous and potentially life-saving to some,” says Mr. Rubenstein. We spend trillions of dollars on clothes, so perhaps it was inevitable that AI would attempt to tackle that age-old question: Do these pants make me look fat?

Being more tuned to geek trends than runway trends, I sought professional help for our tests. Ms. Khavkine, a New York stylist, curated designer garments for Joanna, starting with two date-night ensembles: a shimmering blue jacket with a high collar and a sleek python-print jacket. All four experts preferred the simpler second option. (The blue number “is trying to be contemporary but looks cheap,” Ms. Agins said.) Then Joanna did the sashay and shante in front of Alexa’s judgmental eye. After about a minute, Style Check spit out a result: 70% likelihood the sleek jacket looked better. Consensus!

Then she tried on a pair of black-and-white dresses in very different cuts. Again, our whole panel agreed, picking the dress with a lower hemline because of the way it fit. And, again, so did Alexa, giving it a 68% thumbs up.

In my menswear experiments, aided by Mr. Julch, a San Francisco stylist, we had more mixed results. I modelled the same sweater and pants in two different sizes. The larger size instantly irritated our human judges. Strangely, the Echo Look barely favoured the better fit. That was my first indication Alexa might sometimes be guessing. 

Amazon says the Echo Look tries to give a “holistic assessment” that takes into account fit, colour, styling, season and current trends, as well as “unique characteristics of each customer.” It doesn’t factor in past purchases, a spokeswoman says. “Anyone can use Style Check—whether you’ve purchased clothing on Amazon or not.” The humans who help train the AI are fashion-focused Amazon employees, the company says.

Yet even if we agree on the elements of style, weighting them is subjective. Our judges split with Alexa on a pair of red-orange women’s tops. One had a more appealing colour, but the other was a better fit. Three panellists prioritized fit, but Alexa went for colour.

After reporting its judgment, Style Check asks you to vote on which look you preferred, using the feedback to improve its output. But machines are only as smart as the data they take in, and the Echo Look was lacking potentially important style inputs like location, age—even what kind of occasion the clothes were for.

And, of course, none of that data picks up on how clothes make you feel. I’ve resisted testing my wedding suit with Alexa because I don’t want risk letting a computer ruin my memories.

Can AI Be Fashionable?

Alexa really got off track when I started combining polka dots and stripes. I modelled my favourite custom suit in my standard white shirt and tie, then in a textured shirt, striped tie and polka dot pocket square. Alexa preferred the more conservative look with a 68% rating.

I wouldn’t have come up with the pattern-mixing combo on my own. “It requires you to know a little more about fashion and be willing to take risks,” said Mr. Julch. I liked the polish and confidence it projected. But every time Mr. Julch put me in a bolder look, Alexa chose the tamer option. Amazon says Alexa is equally capable of judging punk outfits and ball gowns. I think that’s impossible, even for a style guru.

Even if a computer had perfect data about the “rules” of fashion—what’s trending, what’s flattering—it would still be lacking, says Genevieve Bell, an anthropologist and professor of engineering and computer science at the Australian National University. “What makes style interesting is usually not the rules, but the breaking of them.” And unlike a fashionable friend, Alexa doesn’t challenge what’s in your closet—at least, not for now. There are companies using machine learning to recommend clothes to buy, and doubtless that’s Amazon’s endgame too. But it will take a lot of data-crunching to match a great store display.

The most useful part of the Echo Look today is how using a camera changes you. With it, you’re more likely to stop and ponder what you actually look like to someone else, even if you don’t agree with the answer.

Digging through my wardrobe, the Echo Look helped me rediscover a long-ignored bright green polka dot shirt, which I compared with a subdued plaid shirt in heavier rotation. Alexa leaned 60% toward the plaid, but I chose the polka dots anyway.