This is a repost of Steve Faktor’s original article on Forbes

To many men, shopping for clothes is like doing your own brain surgery – you’re in no condition to know when you’ve screwed up. Sure, single men must dress up to attract mates. Those poor, unsuspecting women have no clue what fashion nightmares await them. Marriage does to men’s fashion what irritable bowels do to romance. Things get even worse at work. The more casual the office, the more likely we are to see mangled toes and bloated bellies. Even billionaires wear outfits that scream “I sleep in a box.” Of course, it’s the rest of us who need to keep trying. Unfortunately, men’s clothing stores have failed miserably. The shopping experience is hardly painless, especially at department stores. They have the most resources, space, and selection, but they’re packed with men wandering aimlessly like an exiled Judaic tribe.
When I was at MasterCard, I led a project called Total Shopping Solution. Eventually, we commercialized it as two very successful services, Commerce Intelligence and Commerce Coalition. Over the years, I’ve thought a lot about intra-store shopping experiences, especially during all those wasted hours looking for clothes to fit my beefy frame. With today’s technology and some low-tech ingenuity, department stores can reinvent the men’s shopping experience. (After reading this article, I hope they’ll also reimburse me for the the years I’ve lost trying on ill-fitting pants.)
At a conference last week, I noticed something peculiar. A tall man was talking business with a woman well over a foot shorter. The sheer disparity in their size made me realize something really important – that she will never know the joys of finishing a full serving of Chipotle! No, that’s not it. It occurred to me that for all this man’s physical advantages – strength, size, comfortable shoes – he has no empirical advantage in business. In this sterile, white-collar world, where meat comes from ShopRite and homes are built by “guest workers”, men have lost their mojo. Like the Woolly Mammoth and that other guy from Wham!, masculinity is nearing extinction. If the male gender is in jeopardy, it got me thinking about how to turn this trend into an opportunity.



