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Cher Horowitz (Alicia Silverstone) chooses the perfect outfit.
Photo: Paramount

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Digital Closet Startups Want to Give You the Cher Horowitz Experience

As long as you're willing to manually list everything you own.

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In 1995, the world met Cher Horowitz, a rich Beverly Hills babe who “actually has a way normal life for a teenage girl” (so she says, at least) — and while the world of Clueless was populated by a colorful cast of ’90s archetypes whose wardrobes and Valley Girl lilts are tough to forget, it’s perhaps Cher’s closet that, more than two decades later, is the movie’s most memorable supporting character.

“MIS-MATCH!” says the blocky error message on Cher’s computer display as she scrolls through her wardrobe options on an interface that looks better suited for Oregon Trail than high fashion. She finds a matching ensemble (plaid on plaid, naturally), hits “DRESS ME,” and watches as the outfit is modeled on an image of her body on the screen. Satisfied, Cher nods with a smirk — and just like that, one of the most iconic costumes in all of teen movie-dom is born.

Cher Horowitz’s digital wardrobe.
Photo: Paramount

Whitney Casey, co-founder and CEO of Finery, uses Cher’s closet as a shorthand to describe her fashion and tech startup — a comparison that is especially appropriate given the fact that 71 percent of Finery’s customer base falls within the ages of 18 and 34 and came of age in the Clueless era. “I really think that Cher Horowitz should own part of our company,” Casey jokes.

Launched earlier this year, Finery offers a clean, elegant interface that gives its users a place to build their personal closet digitally in a format that they can carry with them. Casey — who came to the business with a journalism background and a love of fashion — sought the development expertise of web veteran Gillis Baxter when it came time to build the platform’s advanced technology, which uses email receipts and store-specific accounts as its primary building blocks. She then partnered with model, actress, longtime friend, and co-founder Brooklyn Decker.

Now comprising 17 employees with nary an official “stylist” among them, the Finery team drew inspiration from tech companies outside the fashion space. If all goes as planned, Casey says the platform will offer to users for their wardrobes what other apps have for their music libraries or finances: anywhere, anytime access. She uses Spotify as an analogy. Just as the music platform allows users to view, manipulate, and interact with their music collection from any device, Finery will give shoppers remote access to their closet. This analogy will be more apt, perhaps, when the Finery app launches in October 2017. The current lack of an app version was a concern we heard from the Finery users we contacted.

Creating an outfit on Finery.
Photo: Finery

Even without an app, Finery has become an almost necessary part of life for Heather Chapman, a 33-year-old hospitality and travel-industry pro who also works as a stylist and blogger part-time. “I use it constantly, especially as it keeps evolving,” she says of the platform, for which she was a beta tester.

“A connected closet is the future,” Casey says. “There's half a trillion dollars worth of clothing hanging in women’s closets all around this country unworn. It’s time to have some innovation here.”

The innovations delivered thus far by Finery use email and store account integration to help users create an online representation of the clothes they already own. When opening a new Finery account, you’re prompted to share your email address and the information for your online store accounts. Finery then sweeps your shopping history, delivering an image of all items you’ve purchased online directly to your connected closet. Pieces that can’t be tracked down that way (specifically, items that were purchased in a brick-and-mortar store) can be added using a Pinterest-style browser widget. Establishing a complete online wardrobe, therefore, does require a fair bit of set-up work, but Casey is confident that once users are operating within the Finery platform and interacting with its other capabilities — a universal wish list, sale notifications, and automated alerts for closing return windows, to name a few — they’ll forget any initial frustrations that may have come with manually adding clothing that couldn’t be added automatically.

Katie Smith, a senior analyst at retail analytics firm Edited, isn’t so sure about those barriers to entry. “The more work that someone needs to do upfront with an app, the more challenging it will be to retain customer loyalty,” she says.

Fay Cowan, brand and content director for Decoded Fashion, echoes Smith’s concerns. “Millennials are time poor,” she says. “In 2017, our biggest luxury is the time we have. Will millennials want to spend the time uploading their entire wardrobes, just so they can identify what’s missing?” Generally speaking, Cowan doesn’t see these technologies “addressing the core shopping habits of millennials.”

Still, Smith notes that platforms that “support the core values of a millennial” may find continued success in the fashion tech space, in spite of the necessary prep work. Millennial shoppers, she says, are particularly interested in personalized, positive experiences that are also fast and convenient. Finery plays perfectly to this audience as a one-stop shop for all things retail. Other more established apps, namely Stylebook, have been successfully carving out their space in this sweet spot for several years. According to its website, Stylebook now includes more than 90 features, all of which support the platform’s goal of helping users “get the most out of what you already have in your closet and to choose new pieces that will integrate well into your wardrobe as a whole.”

Just five months out from the platform’s general launch, Casey reports 30,000 users have already signed up for the much younger Finery — a number that, she says, is “pushing fast.” Next up? The team will launch its app, then continue working on an advanced recommendation engine that will give the platform styling capabilities without the necessity of human stylists. They also hope to develop marketplace and wardrobe-sharing features.

At this point, Finery is free to its users. While similar-but-different platform Cladwell charges a monthly subscription fee, it’s already tackled the outfit-recommendation engine and app capability that’s still around the corner for Finery. Launched in 2012 in its original iteration — which offered its then-male-only users personalized recommendations and ran on affiliate fees — Cladwell now provides its subscribers with shopping and dressing guidance according to the logic of a capsule wardrobe. Unlike Finery and many other fashion-centric platforms, Cladwell is brand-agnostic, focusing instead on directing people to arrange the items in their closet according to more general characterizations. (Do you have a white, V-neck, short-sleeved shirt? Do you own a pair of gray pants? Cladwell prompts you to populate your online wardrobe by checking off these kinds of descriptors.)

Blake Smith, Cladwell’s CEO and co-founder, really doesn’t want to sell you clothes. “We never talk about where to buy anything,” he says. “We focus on what to wear every morning, how to build a more interchangeable wardrobe, and what to consider buying in the future, but we never close the sale.”

Like Finery, Cladwell runs on advanced technology built largely by a team of fashion outsiders. Smith — whose training and background is in computational mathematics — built out algorithms on paper and worked with developers to make them a digital reality. Once users have been “onboarded” into the Cladwell universe, they’ll receive daily outfit recommendations based on the items they’ve logged into their wardrobe, as well as the local weather forecast. The technology also learns more over time and as it’s given additional information. Tell the app what you wore on Tuesday, for example, and it won’t recommend anything similar for you on Thursday.

While this daunting and potentially time-consuming idea of “onboarding” seems like a potential stumbling block for Cladwell, just as it does for Finery, Smith is confident that his product’s value proposition is strong enough to overcome it. Potential users who aren’t sufficiently fed up with staring at their closets and struggling to come up with a great outfit (“too many clothes and nothing to wear,” to put it simply) that they want to take the time to get set up on Cladwell, he says, aren’t his customers — yet.

“I do think there is something in the ethos behind Cladwell, but it looks like too much work for the customer from the off,” Cowan counters. “We see a lot of startups … and onboarding needs to be simple and accurate, particularly when you are asking the customer to change their habits.” She muses that the app would benefit from a “concierge commerce” experience: a Cladwell team member who could help users physically execute a “closet cleanse” before diving into the platform.

Photo: Sofie Delauw/Getty Images

Katie Smith’s greatest concern about Cladwell’s long-term viability is its lack of brand-driven variety, but she also acknowledges that capsule wardrobes have been one of the hottest recent trends among bloggers. The app might just be in the very right place at the very right time.

Customer reviews for Cladwell in the iOS App Store seem to reflect both the great opportunities and great potential challenges for emerging platforms in this space. While the average rating is two and a half out of five stars, individual ratings skew toward five and one stars, leaving few customers in the middle. At this stage, Blake Smith characterizes the company as “scaling.” He notes that they’re investing big bucks in marketing and seeing returns on that investment. Cladwell has maintained users since its original 2012 launch, and it has a serious fandom. Elaine Wakely, a 35-year-old CPA, management consultant, and mom of two, uses the app daily and has been so inspired by it that she dedicates an entire Instagram feed to her capsule wardrobe.

“I don’t have time in my life to waste shopping and trying on clothes that don’t fit me right or that I don’t love,” Wakely says. “That is all time that can be spent earning more at my career or [with] family and friends. Cladwell helps me be intentional about my wardrobe and style.”

Similarly, Casey says that Finery’s position as a “productivity tool” for fashion is proving to help many of its users spend less and shop more intentionally. “I think being able to view your own clothes the way you would shop in a store satisfies the urge to shop aimlessly,” says Sarah Rockett, a 34-year-old children’s book editor and Finery fan.

Even self-professed “out of control” shopper Chapman tells us that she is shopping “smarter” now with Finery on her side — and the platform fits perfectly into the busy schedule that has driven her to make most of her purchases online. “I rarely, if ever, go into an actual store these days,” she says. “Just the thought of it makes my stomach hurt!”

Given the insights from Edited’s data, Champan’s online habits come as no surprise to Katie Smith — or to Lisa Bougie, the GM of Stitch Fix Women, a platform that arguably set the standard for styling and wardrobe platforms. “Our clients love that we do the shopping for them,” she says. “In terms of ease and convenience and creating time in our clients’ lives to do the things that they love that aren’t shopping, it’s also a huge bonus.”

According to Bougie, Stitch Fix — which launched for women in 2011 and has since expanded into petites, maternity, plus, premium brands, and men’s — uses a mix of highly developed algorithms and human stylists to develop the Fixes for each client. “We allow and support machines to do what they do best, and people to do what they do best,” Bougie says of the Stitch Fix model. It’s worth noting that both Cladwell and Finery have opted (at least for now) to exclude the human styling element.

Whether the looks are styled by human or machine — and whether or not the process of “onboarding” new users onto platforms like Finery or Cladwell eventually proves too great of an obstacle for growth in the future — at least for now, platforms like these seem to have captured the attention and imagination of a large enough user base to move the needle and inspire continued investment. Why? Again, we look to Clueless.

“I think any technology or platform that helps women save money, save time, and feel more satisfied with their wardrobes can have staying power,” Rockett says of her Finery experience. “Plus, it makes me feel like Cher from Clueless. So, that’s a win.”

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