Trunk Club: Your personal fashion expert, via webcam

I hate shopping for clothes. Hate it. Given the choice between the dentist's office and a dressing room, and I'd probably pick the dentist. That's why I love the idea behind Trunk Club, a new site that boasts a squad on online fashion consultants offering personalized shopping for guys—like me—who are allergic to clothing stores.

Trunk Club, which launched earlier this week, lets you meet with a trained fashion expert online over Skype—all you need is a webcam, plus about 12-15 minutes for a "discovery session," during which your personal shopper will quiz you about your lifestyle and sartorial likes and dislikes.

Don't worry—you won't flunk the chat session if you're not up on the latest fashion trends. "Part of our job is to infer what a guy would like," says Trunk Club CEO and founder Joanna Van Vleck. "We don't ask questions like, 'Do you like a spread collar or a linen collar?'" Instead, expect easy (but revealing) questions like, "Are you married," "Do you have kids," and "What do you do for a living?" And, of course, they'll help you figure out your size.

About a week later, you'll get a shipment of brand-name, hand-picked outfits sent to your home or office; then you connect with your Trunk Club expert via webcam, try on your new duds, and discuss. Don't like what you got? Send the kit back with the pre-paid shipping label, and your Trunk Club expert will try again with a new selection (and you can repeat the process as often as you wish). Like what you see? Then you're all set.

One of my first questions for Trunk Club founder Van Vleck is how much the service costs. The answer: Nothing, except (of course) the retail price of the clothes you choose to keep. Trunk Club buys its clothes (brand names all, I'm assured) wholesale and makes its money off the standard retail markup (which you'd normally pay at, say, The Gap or Neiman Marcus). Shipping—both ways—is free.

As for the Trunk Club fashion experts, Van Vleck says there are 21 now, and the site expects to add between four and six new experts a month. And no, they're not just random clothes-horses with webcams; they're culled though a "rigorous" selection process, and each has undergone on-board training and a three-month mentoring program, Van Vleck said.

Trunk Club is targeting only men for now, although the company has "started discussions" about a version of the site for women.

Of course, the proof of all this is in the pudding, so I'll be putting myself in Trunk Club's hands in the next week or so. Expect a full report on my test drive shortly, complete with before-and-after photos. (I need to go clothes shopping anyway, so ...)

OK, so what do you think: Who here could use an online personal shopper?