Menswear E-Tailers Peddle Salvation in a Box

Steven Kaplan dreads everything about department-store shopping: the too-loud music, the harried salespeople, the 10 or more brands of identical pants and shirts. The good news is, he never has to go back. “I will literally just go online, push a button, and have something that fits delivered to my door,” says the 31-year-old music entrepreneur. The Brooklyn resident recently signed up with Bonobos, a menswear e-tailer that made its name marketing pants tailored to different body types. “I need someone to tell me what to wear and remember me.”

Fashion is the fastest-growing segment of online commerce, and its growth is being propelled by men. Like Kaplan, more and more guys are fleeing malls and department stores and flocking to websites that claim to have taken the pain out of shopping. Sites such as Bonobos and Thrillist are capturing a bigger share of the $41 billion U.S. fashion e-commerce market with services such as personalized recommendations based on purchase history or brief online surveys. Some will ship a trunk of clothes to a man’s home, so he can pick out the items he likes and return the rest free of charge. “Men don’t hate fashion, they just hate shopping the way it’s designed for women,” says Ben Lerer, co-founder of Thrillist, which bills itself as a “digital lifestyle publication” for men. “The young generation of guys love to shop, they love to talk about the brands they like, and they really care about how they look.” To cater to this demographic, Thrillist acquired the e-tailer JackThreads.com in May.