Reviving the Digital Wardrobe – Lookbook's Gen Z Approach to Personal Style

Written by: Steve Beyatte

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In 1995’s Clueless, long before the iPhone brought the touchscreen into public consciousness, Cher Horowitz taps on a glowing monitor that rotates through her wardrobe, visualizes her wearing the outfit, and like any good friend, stops Cher from committing a fashion faux pas. The scene lasts less than a minute. But thirty years later, that fictional wardrobe remains more culturally relevant than any real-world attempt to build one.

The industry has tried. In the 2010s, apps like Stylebook and Cladwell promised to digitize closets and help users with outfit planning. More recently, platforms such as Whering reframed the concept for a sustainability-minded generation. Hundreds more have come and gone. Yet, none have broken out into mainstream social consciousness outside of niche fashion circles.

“There hasn’t really been a digital wardrobe that’s taken over the broader population,” says Max Hui, cofounder of Lookbook, a new entrant in this space. “These apps haven’t achieved the cultural relevance that Instagram or Snapchat, or even social media phenomena like BeReal or Fizz, have.”

Chen (left) and Hui (right) pose for a street-style photoshoot for Lookbook's marketing presence.

Hui, chief operating officer at Lookbook responsible for the company’s product strategy and marketing, says it is important for players to understand why the landscape has historically been this way. “Many people would love the benefits that existing digital wardrobe apps provide, but the cost of onboarding is far too high.” According to Hui, across hundreds of interviews with users, only one or two people were actively cataloging their clothes on existing digital wardrobes. “There are even people who are turned off of Beli [a popular restaurant-logging app] because it asks you to rate 10 restaurants, and even that small onboarding hurdle is enough to turn users away.”

Hui has a keen eye for this kind of user friction: before Lookbook, Hui led an operations research team at the engineering consultancy EKN Engineering, where he scrutinized the process of onboarding institutional clients onto their software platform. Hui found that by thinking from the ground up and applying emerging language models to eliminate the most tedious tasks, his team could cut hundreds of man-hours from each client’s onboarding experience. “Disengagement happened when we asked users to do too much before delivering value to them,” Hui recounts. “As it turns out, this problem for enterprise software is also a problem for Gen Z’s digital wardrobes.”

An outsized onboarding hurdle is not the only stumbling block for apps trying to break into this space. Hui believes that broader cultural shifts around technology are also complicating adoption. Despite the increasing share of consumers who have grown up with screens as a part of their lives, Hui doesn’t think users are necessarily more comfortable with their lives being interpreted by software, noting that users are becoming “increasingly intentional” with how they engage with tech. “People are coming around to the idea that analog is better,” he observes, describing the dopamine-driven design of many popular apps as “addictive” and leads to users regretting their time spent on them.

Where so many players have tried and failed, one might wonder what it would take to succeed.

Hui presents the case for a new kind of fashion tech to investors at The Residency's demo day.

Hui is confident that Lookbook has what it takes. His thesis? That, as Gen Zers, his team understands the needs and whims of their generation. Hui believes that Lookbook’s younger demographic, though more cognizant of how they use technology, already exhibits the habits that earlier apps have tried to artificially manufacture. He singles out one habit as an example: taking outfit pictures. “That’s a behavior we want to tap into because it’s already a part of their routine,” says Hui.

He also points out the desire for young adults to learn about themselves and discover the vocabulary to express their own identity through different avenues: food, music, exercise, and of course, clothes. “We’ve found that users love to learn about themselves, what colors they like to wear, what styles they prefer, what items they wear most, what they like to pair with each item,” recounts Hui. He points to Spotify Wrapped as an example of this desire for self-understanding, a year-end summary for users of the music streaming service that has now become an annual ritual that draws hundreds of millions of interactions every December. Hui says the team studied why those reflective features resonate, and applied similar principles to Lookbook’s design.

Hui and Chen rehearse for a short-form video bound for Lookbook's social media accounts on TikTok and Instagram.

There are other Gen Z-isms that Hui is counting on as well. Hui creates content on a joint TikTok account with his cofounder, Avery Chen. Running the account and growing it to a viewership of over a million people, Hui says, gave the team a close view into how quickly digital behaviors scale, and how quickly users disengage from what feels forced, often in under two seconds for a short form video on social media. Manually organizing a digital closet, in Hui’s view, is also one of those forced behaviors: “Organization becomes labor when users have to go out of their way to do it, when they have to find the volition to do it.”

Lookbook attempts to remove that labor almost entirely. Rather than asking users to photograph and tag individual garments, the app begins with outfit photos, images users already take. From there, software groups repeated items, detects patterns, and quietly builds a wardrobe without the user lifting a finger.

Aside from reducing the practical obstacles that have traditionally plagued digital closets, the more provocative question is whether software should be interpreting personal style at all.

Historically, taste has been positioned as something that’s instinctive, cultivated through exposure, subculture, intuition, as almost an antithesis to what the tech industry represents. Taste remains an elusive facet of the human experience that hasn’t yet been cracked by the relentless advance of software development, a position increasingly voiced by leaders in the tech industry. Does approaching style as a science, then, sharpen, or flatten, taste?

Hui is clear that self-expression, not technology, is what Lookbook is after. “Everything we do is to help you, the user, explore your own style. The last thing we want is for a computer to replace taste, and we’ve intentionally designed experiences where that doesn’t happen.”

He recounts how one Lookbook user discovered she was relying on one color more than she wanted, and as a result, began experimenting with new styles she wouldn’t otherwise have tried. Another user found that having a count for how many times certain pieces were being worn helped them decide whether to let those pieces go.

These experiences run counter to much of the past decade in tech, where AI largely accelerates and dictates consumption through algorithmic feeds, targeted ads, and attention capture. According to Hui, his goal is to offer users an avenue where this technology can instead drive self-reflection and discovery.

Whether this approach resonates with users depends on a broader cultural mood. As trend cycles compress and aesthetics are pushed to media feeds, taste can become increasingly externalized, dictated by algorithms rather than discovered internally. In that environment, a tool that surfaces personal patterns may offer a counterbalance that resonates with those developing their own sense of style.

That, at least, is their bet.