This New Styling Service Is Part Stitch Fix, Part Clueless Closet

As Stitch Fix tries to reverse its fortunes, a new hopeful is breaking into the online styling market with AI tools, a new chief technology officer fresh from Gap Inc. and a new proposition that will compete with the onetime fashion unicorn by providing stylist advice to a key demographic — Millennial moms.

Called LookingGlass, the Austin-based business targets the Millennial mom market, and is in position to finally give fashion a modern version of the long-awaited “Clueless” closet — the automated wardrobe made famous in the 1995 Alicia Silverstone film.

The on-demand styling business, founded by nurse-turned-stylist Lana Ashby Rowder, was conceived to fill a gap she identified in her personal life, she told WWD, by focusing on the “Millennial mom” market.

“I stayed at home to have kids and, like, woke up and was like, ‘I don’t even know my new body,’” she said. “I don’t even know what to wear anymore. I’m used to this pre-baby body and wearing scrubs every day in the hospital, and now I’m going to PTA meetings, luncheons, galas and all of these things for my new life, and I just really found this huge hole in the market.”

The business began as a mobile app that, Rowder admitted, “wasn’t built very properly,” and was even targeted by scammers. So she went back to the drawing board with a web offering, based on feedback from its hundreds of downloads — many of which complained about “app fatigue,” she said.

“I want to perform the styling sessions just like I do when I order Uber Eats or order my groceries,” Rowder added, channeling her customer feedback. “And so that’s what we’ve built.”

Like many tech-driven styling platforms, LookingGlass relies on a mix of artificial intelligence and human effort. But not in a way that overshadows its people-driven styling expertise.

For now, the company is developing AI as a tool that makes closet-scanning less of a chore.

The concept is to allow users to photograph a couple of items to ask for help, even take video of several pieces. All the while, the system identifies and catalogues the apparel, so that over time, the entire wardrobe gets indexed.

“Our product will be able to send our members daily outfits where we’re like, ‘Hey, it’s 75 degrees in California today. Where are you going?’ and you say office, gym, supermarket, etc.,” Rowder explained.

”You let us know, and we spit out a great ‘Here’s what you’re going to wear’ [recommendation]. Those items are all going to be from your current wardrobe.” Consumers will also be able to connect directly with their stylists on an as-needed basis, with subscriptions from $95 and up (monthly), starting with roughly an hour of styling per month.

To help build all of these features out, LookingGlass just brought in a new chief technology officer, Deven Alimchandani, who previously ran software teams at Gap Inc. after various stints at tech and retail companies, including Macy’s and eBay.

Alimchandani joined because he was impressed with the company’s vision and business model, he told WWD: “I have an exceptional opportunity to strategically blossom the vision and innovate next generation technology to create smiles and save the planet for alpha and Z generations.”

Helping users make the most of their closets supports fashion sustainability, and brand partnerships can ensure stylists can fill any holes in a given wardrobe. Eventually, more of the suggestions will be driven by data intelligence, according to Rowder, and as the business expands, it will explore new areas — like men’s styling.

In fact, she said, the platform just logged its highest number of male users last month.

Apparently all kinds of consumers want on-demand styling help. “I don’t want to spend a bunch of money and do this overwhelming closet,” Rowder continued. I just want someone to tell me what to wear now, and there’s nothing out there where you can instantly connect with a stylist. That’s just not available.

“Stitch Fix has something where you can email and they’ll get back to you…we feel like that’s just another confirmation that we’ve got product market fit.”

Soon, the founder will be hitting the fundraising circuit, so she’ll see if that pitch resonates as much with investors as it did with Alimchandani.

From the new CTO’s perspective, LookingGlass demonstrates a fundamental truth about AI.

“Artificial Intelligence is at the center stage of everything,” he said. “In the next few years, as standards and regulations normalize in the best interest of humanity, AI will simplify many more things, so people get time back to enjoy nature’s gifts.

“The LookingGlass team is on this journey to digitize and simplify routines.”