Flash Forward with JackThreads

JackThreads CEO Mark Walker; Crevo for JackThreads “Bookham” boots, $95; JackThreads “Skinny Stretch” selvage jeans, $99; Publish for JackThreads “Carden” anorak, $169. / Courtesy Photos

Since the days of dial-up, online shopping has been hailed as a godsend. Yet the harsh reality is that it can turn even the simple task of buying clothes into a leap of faith—a prohibitively pricey one for young consumers when you consider the up-front costs and shipping charges. “With millennials, it’s more about bang for the buck,” says Wellesley-based fashion-industry vet Mark Walker. As CEO of the boundary-pushing men’s apparel website JackThreads, he’s found a new way to target budget- and style-conscious shoppers: by bringing the dressing room to them.

Known for its low prices on trendy brands, JackThreads is now courting the millennial shoppers who make up 78 percent of its audience with its ultra-convenient TryOuts system, launched this year. While most fashion sites charge first and refund returns later, TryOuts allows you to order as much merchandise as you want, sending it out without charging a dime. You have a week to try things on and send back any duds that don’t fit—and, yes, JackThreads pays for return shipping, too. “We don’t want any of your money until we know that you’re 100 percent confident in what you got,” Walker says.

It’s fitting that JackThreads is trying to reinvent digital commerce, considering how swiftly the company has reinvented itself. Launched as a flash-sale menswear site, JackThreads was snapped up by Thrillist Media Group in 2010. When Thrillist CEO Ben Lerer wanted to steer the business in a different direction in 2014, he pulled in Walker. After spending 15 years with Gap, Walker had plenty of brick-and-mortar retail experience; he’d also learned the ropes of e-commerce at the Fort Point–based discount-fashion site Rue La La. “I saw the writing on the wall that flash was kind of dying,” he says. Since his arrival, Walker has overseen a complete overhaul of the brand and the launch of JackThreads’ own clothing line.

With the success of TryOuts, more changes are on the horizon: Walker soon hopes to roll out completely assembled outfits. “JackThreads is already sitting in what I call ‘the next frontier of retail,’” Walker says. “The sky’s the limit.”