Gadget Hound tries Trunk Club on for size, likes how he looks

Remember Trunk Club, the new, online personal shopping service for men who hate shopping for clothes? Well, given the fact that I am, in fact, one of those shopping-averse guys, I figured I'd give Trunk Club a try for myself. Two Skype calls and three outfits later, I'm looking a whole lot snappier.

Before I launch into my story, here's a quick refresher. The Oregon-based Trunk Club launched just this month (you can find it here), and it boasts about 20 online experts (all of whom have undergone a "rigorous" selection process and three months of training, according to CEO Joanna Van Vleck) who meet with you via Webcam, assess your sartorial needs and size, and send shipments of new clothes for you to try. Trunk Club doesn't charge membership or service fees; instead, it buys clothing wholesale and makes its money on the (competitive, I'm told) retail markup. You only pay for the clothes you decide to keep.

So here's how it works, starting from the top: You sign up with the service right here and enter some basic personal information, including your marital status, whether you wear "business casual" or "business formal" at the office, and why you're looking to join Trunk Club. (Don't worry: Unlike Fight Club, there's no rule against talking about Trunk Club.)

Within about 24 hours, I was e-mailing back and forth with Lisa, my designated Trunk Club expert, and we set up a Skype appointment—our introductory meeting—for the following week.

Now, I was a little nervous about my first Trunk Club video call—partly because I'd never really video conferenced before (I know, I know, I'm way behind when it comes to Skype), and also because … well, what do I know about clothes? How would I answer a question like, "What kind of wardrobe would you like to have?" Um, beats me. All I know is that my closet looks like the J Crew catalog circa 1994.

Anyway, the morning of our Skype video call arrived, I fired up the Webcam on my MacBook Pro (Trunk Club will send you a free Webcam if you don't already have one), and I was face-to-face with my fashion nemesis, Lisa, who I figured would take one look at my baggy shorts-and-polo shirt ensemble and sneer in disgust.

Well, to my great surprise, Lisa turned out to be friendly, engaging, and totally charming. Within a few minutes, we were comfortably chatting away, and my fears of being grilled about my fashion sense—or lack thereof—subsided.

Instead, Lisa (yep, she's pictured here) looked me over (nope, no sneering that I saw) and asked me a few simple questions: Is this what I usually wear at the office? (Yes, thanks to the lax dress code in my kitchen.) What are three words I'd use to describe myself? (I had a little trouble with this one; funny? loner? shy? I couldn't come up with three words on the spot, but no problem.) What do I have in my closet now that I don't like? (Where do I begin?)

Next, I gave Lisa a few basic measurements. Raiding my closet, I rattled off some shirt and waist sizes. I tried on an old blazer (waaayyy too big, as it turns out) and read the tag inside. I held some of my shoes up to the camera, along with some belts.

Finally, we talked about what I wanted to fix in my wardrobe … a conversation that wasn't as tough as I thought it would be. Mainly, I was tired of looking dumpy compared to my fellow New Yorkers, or feeling like a 15-year-old during vendor meetings. That said … I wasn't interested in looking like I worked on Wall Street. (No offense, Wall Street folks.)

And with that, we were done. The typical introductory Trunk Club Skype calls takes about 15 minutes, I'm told; Lisa and I chatted for closer to an hour, but to my surprise, I enjoyed myself.

We scheduled another Skype call for a week later, and in the meantime, I waited for my "get to know you" box—a shipment of outfits selected by a team of Trunk Club clothing pickets, under Lisa's supervision—to arrive at my doorstep. (Shipping is free, both ways.) The clothes in the "get to know you" box aren't intended to be perfect choices; instead, they help your expect (or Lisa, in my case) gauge what you like and don't like, as well as what fits and what doesn't.

A few days later, a Trunk Club employee called and asked for my credit card number, explaining that she needed to authorize my card before the clothing arrived. Reasonable enough (in case, for example, I decided to keep the clothes and never call back), but I had to give my info over the phone—not the most secure method of payment, if you ask me. That said, my understanding is that Trunk Club (which only recently went out of beta) will soon (if it doesn't already) have a secure, online method for submitting your credit card info.

Anyway, the "get to know you box" arrived, with three outfits: Three shirts (a white striped polo, a brown striped button-up, and a blue checkered button-up, all Ben Sherman), three pants (a pair of "squiggle" straight-leg jeans by Seven for All Mankind, and two pair of Bonobo slacks), and a thick leather belt (Tornio). If you're wondering how I knew all the brand names, well … I don't, I'm just reading off the packing slip—but from what I've been told, these are pretty cool (but not exorbitantly expensive) labels.

With my wife in attendance this time, I launched another Skype call with Lisa and began trying on clothes … and guess what? I loved what I was wearing—and more importantly, my wife was delighted. The new shirts were a bit snug, but (as I now know) that's how they're supposed to fit; I'm just used to huge XL polo shirts and baggy jeans from the 90s. The slacks and the jeans fit great, too (although the slacks might need to be taken in a bit), and the new leather belt put my ratty old belt—my favorite, of course—to shame. (After showing Lisa my tattered, probably 10-year-old belt, my better half made the unilateral decision to toss it in the nearest Goodwill bin.)

So surprisingly enough, my "get to know you box" was, in fact, three-for-three in terms of outfits, and I ended up keeping all of them. The total: about $735, which is actually pretty reasonable for seven snazzy articles of brand-name clothing. (And yes, I'm paying with my own money.) As I understand it, if you're on a budget, you can tell your Trunk Club advisor and he/she can make their picks accordingly. 

Would I do it again? Oh yeah—in fact, I'm having another Skype appointment with Lisa next week (for casual summer shoes and shorts, this time). Turns out shopping for clothes—over a Webcam, anyway—isn't so bad after all.