For these fashion retailers, innovation finds the perfect fit

These startups are using the latest technology and integrating customer feedback to make online shopping easier

As the weather cools down, shoppers review their closets, looking to fill any gaps in their own wardrobes and preparing their children to go back to school. Direct-to-consumer apparel companies—which bypass traditional bricks-and-mortar stores—evaluate trends in shopping habits and find a way to make tasks easier on consumers.

Three startups are using technology and integrating customer feedback to do just that. One helps men buy unique, perfectly fitting shirts; another looks to easily fill what may be a guy’s most important (and most ignored) drawer; and a third assists parents in properly sizing their kids’ feet to make online shoe-shopping easier.

Every great outfit starts with what goes under it, but Laura and Michael Dweck (29 and 31, respectively) know that most men don’t want to spend a lot of time and effort shopping for socks and underwear. So in 2015, after a post-honeymoon fight over Michael’s overstuffed underwear drawer, they started Basic Outfitters, “an online destination for men to refresh their basics drawer in under two minutes,” says Laura, the creative director. For $60, customers can select a pack of socks, a pack of underwear, a pack of T-shirts and a “wildcard basic”—jogger-style pants or an extra set of socks, underwear, or tees. (The success of the company—it now has a team of 10 working out of its office at WeWork 135 Madison Avenue—landed the founders on the Forbes 30 under 30 list.)

“All couples have the same complaint about a significant other’s drawer,” says Laura Dweck of Basic Outfitters.

Basic Outfitters quickly learned customers couldn’t be grouped into “basic” or “fashion” categories, so the wares come in a variety of styles. Even if a guy initially chooses plain socks, Laura said, he’ll often go for a bonus pack of the popular “micro-conversational” prints for socks or boxers, which feature prints like motorcycles or palm trees. And sometimes male stereotypes do turn out to be correct: Basic Outfitters’ customers can’t get enough blue, but yellow regularly remains on their virtual shelves.

Laura has learned perhaps more than she ever expected to about men’s underwear preferences—Basic Outfitters followed early feedback requesting boxer briefs with a fly opening, and their popularity persuaded the company to develop more such styles.

Taking fashion risks

Woodies Clothing, which sells custom button-down shirts (starting at $85) and chinos (starting at $98) from its website, also discovered that men are willing to take fashion risks, even with  collared shirts. While Woodies’ bestsellers include straightforward no-iron blue and white button-downs, a flamingo-print shirt sold out in its first run. “That’s something we were not expecting,” says founder Jacob Wood, who works from 175 Varick Street in Lower Manhattan. Since moving into WeWork in 2014, Woodies has expanded to a staff of five.

Customers may be pleasantly surprised by how extensively Woodies has streamlined its process of ordering a custom shirt, which involves a dizzying number of options for collars, cuffs, and pockets. When Wood, a former buyer at Macy’s, founded his company in 2014, early iterations of the site suggested that customers use a tape measure and watch videos to take their measurements. Needless to say, that idea didn’t fly.

With height, weight, and average shirt size, we can extract all your measurements and send you perfect-fitting shirts,” says Jacob Wood of Woodies.

Now, the 31-year-old entrepreneur says, “we have an algorithm: With height, weight, and average shirt size, we can extract all your measurements and send you perfect-fitting shirts.” Pant sizes can similarly be determined when the customer provides his waist size.

Kicking around an idea

One startup is trying to make shopping for kids’ shoes easier for parents. Growing kids’ sizes are always changing, and it can be difficult to get those growing kids to cooperate in a brick-and-mortar store. So Jenzy‘s app directs customers to snap a picture of a child’s foot next to a credit-card-sized card (preferably one that doesn’t show financial information, like a library or store loyalty card). The app, which serves kids up to 6 years old (there are plans to extend the age range), then recommends the best sizes for the child in various brands and styles, including those from well-known manufacturers like Keen and Pediped.

“We’ve been live in the app store for about two months and have about 1,500 downloads,” says Carolyn Horner, who cofounded the company with Eve Ackerley. The two are very pleased with their return rate.

It was not the most obvious path for the two child-free 20-somethings, but as they thought about starting their own clothing company, they kept hearing from friends who were frustrated with buying children’s shoes online. They realized that they could simplify the process.

Development of the app involved a lot of trial and error for Horner and Ackerley, who met teaching in China after college and are now based at WeWork 1601 Market in Philadelphia. Well before they were ready to send it to mommy bloggers for review, they found a surefire way to entice fellow WeWork members to test-drive the app in the building’s common areas. “We’d bring doughnuts to the beta test,” says Horner. Not only did they meet parents who offered suggestions, they got acquainted with a graphic designer who ended up doing the UX for their site.

The founders of Basic Outfitters also picked up tips from the WeWork community. One particularly lucky break, Laura Dweck says, was meeting a video producer in the WeWork building who agreed to shoot a series for social media to build buzz. “He put together some incredible footage, taking influencers around the city to film people going through their life wearing our basics,” she says.

The experienced producer, who’s done work for brands such as Bravo and Chevrolet, simply believed in the product. Laura says she recalls him saying, “I’ll do this for you guys—let’s have some fun.”

Dweck says the producer gathered some social-media influencers and filmed them going about their days in Basic Outfitters attire. Soon the company was getting notes from people who loved the clothing, including some women who wanted it to expand its product line.

“All couples have the same complaint about a significant other’s drawer,” says Laura. “We started the company to help out men, but now the demand for a women’s drawer is off the charts.”

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