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“Alexa, Is It Dorky Or Cool To Wear Sneakers With Khakis?”

Skype interview? Hot date? Perry Ellis is turning Amazon’s virtual assistant into personal men’s stylist for every occasion.

“Alexa, Is It Dorky Or Cool To Wear Sneakers With Khakis?”
[Photos: courtesy of Perry Ellis, Amazon]

My dad had two standard-issue outfits: A suit for work, and a polo-jeans combo, sometimes with a sports jacket, for the weekends. Between those two styles, he was set for pretty much any event and always looked dapper.

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But the clothing landscape has changed, and dressing has increasingly gotten more casual. On the plus side, this means being more comfortable, but it also leads to more head-scratching decisions about what to wear. For men, those decisions can mean staring blankly into your closet, slightly paralyzed with indecision. If your office has a relaxed vibe, can you wear sweat pants? Is it dorky or cool to wear sneakers with khakis? And how the heck do you know when slim fit pants are too skinny?

These are questions that style-conscious men deal with every day, and now Perry Ellis is coming to the rescue with a voice-activated personal stylist that works through Amazon’s Alexa.

In a survey that Perry Ellis conducted of more than a thousand men between the ages of 18 and 53, 81% reported having trouble getting dressed for an event, while 73% admitted to arriving at an occasion feeling inappropriately dressed. “As we spoke to our customers, we realized that the increasing casualization of clothing can be confusing,” says Perry Ellis president Melissa Worth. “Our typical customer is around 30 years old and is very tech-savvy, so we decided to use technology to help solve this problem.”

[Image: courtesy of Perry Ellis]
Starting today, when you’ve downloaded the “Ask Perry Ellis” skill, you can wake up in the morning and say, “Alexa, ask Perry Ellis what I should wear today” to get very specific recommendations. If you’re going for a Skype interview, for instance, Alexa might suggest a “slim striped shirt, a slim suit jacket, and boxer briefs.” (Pants are obviously irrelevant on a video call, so might as well be comfy.)

Perry Ellis also made sure that Alexa tailors outfits to the specific wearing occasion–150 of them, in fact. You can tell Alexa that you are going to a beach wedding, on a first date, to a birthday party, or just to the office, and receive plenty of recommendations. “It’s not just that clothing has become more casual,” says Perry Ellis creative director Michael Maccari. “It’s also that men are living very busy lives and need to change their outfits based on each wearing occasion. It’s hard to know what looks appropriate anymore.”

All of the outfit suggestions will be drawn from the Perry Ellis catalog, but users don’t necessarily need to have those specific pieces in their closet for the tool to be useful. The suggestions are meant to offer inspiration so men have a better sense of how to pull a look together. If the first option doesn’t fit the bill, you can ask for more recommendations. Of course, if you’re actually interested in buying a particular item, you can make the entire purchase while talking to Alexa.

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[Image: courtesy of Perry Ellis]
According to Worth, Perry Ellis chose to develop this tool through Amazon’s platform because Alexa is currently the most widely adopted personal assistant, with 70.6% market share, according to eMarketer. The brand will see how consumers engage with it, then consider whether it is worth expanding to other systems, like Siri. Perry Ellis will also gather insights from the questions men ask, to improve their products and how they interact with consumers. If men are consistently asking for recommendations for, say, what to wear to an office barbecue, this might be a cue that the brand should feature stylish barbecue outfits on its homepage.

About the author

Elizabeth Segran, Ph.D., is a staff writer at Fast Company. She lives in Cambridge, Massachusetts.

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