Men: Can a Stranger Dress You Better Than You Dress Yourself?

Trunk Club delivered clothes

Fashion thrives on the tangible. That old proverb “seeing is believing” is of crucial importance when it comes to clothing. But there’s a little piece of all of us men that wishes someone would do it for us — pick out an outfit, top to bottom, just like our mothers (perhaps regrettably) used to do for us in our elementary school years. 

Over the years, I’ve been lucky enough to have help picking out new clothes–from my mother, sister and girlfriend, among others. But a few months ago, I received a box of clothes in the mail, a package that had been tailored specifically for me–filled with stunning outfit choices from Theory and Ben Sherman, no less–and selected by none other than Lisa Bubes.

Who is Lisa, you ask? To be honest, I’m not entirely sure. Lisa and I have no history together. In fact, we’ve never met in person and have only spoken on the phone twice. But she demonstrated an incredible ability to both match and challenge my personal style brand, presenting me with four highly-curated outfits in colors and styles that suited me precisely. And it was all done from the comfort of my desk, with no need to trek from store to store in the frigid New York winter, hunting for whatever garment I happened to need.

The fashion-filled box that arrived was all part of my experience with Trunk Club, a subscription fashion service that assigns each customer a personal stylist and a fashion consultant via phone or Skype. After sizing me up, figuratively and literally, the very bubbly, exuberant Lisa went to work, selecting outfits that fit my size (I’m slim, so clothes are often baggy on me) taste (I don’t like brown or horizontal stripes) and budget (So I might have said there was no limit here). Some of these outfits were exactly what I’d be looking for in my local Macy’s or Nordstrom. Others — like a shawl-collared sweater and a moorland sweater — are clothes that wouldn’t garner a second glance (let alone a first) if I were shopping for myself.

Curator and Mule / “We find it, you rock it”

And the emerging Internet-based service economy has made it easier than ever to shop without having to even get dressed (surely ironic for a company like Trunk Club). After my experience with the Chicago-based company, I found there are many others with similar business models. I looked into five total services that offer fashion subscriptions, each doing it slightly differently. Aside from Trunk Club, which assembles a massive box for you upon request, Bombfell sends you a single item each month, Five Four Club makes its own clothes, Curator and Mule sends accessories only, and Frank & Oak lets you choose exactly what clothing items you’re getting. On the pages that follow, we’ve reviewed each service.

Before I paint myself as some sort of clueless schlub, I must admit: I consider myself relatively fashionable, and have heard similar positive words from friends and coworkers; my only critique would be the relative banality of my day-to-day outfits. To account for this, I would invoke the typical male excuse: lack of inspiration and creativity. Shopping can be dreadfully tedious for men, something proven by studies over the years. A 2007 study from the Wharton School of Business at the University of Pennsylvania observed that “women are happy to meander through sprawling clothing and accessory collections or detour through the shoe department.” On the other hand, men are on the hunt for one item and one item only, wanting to get in and get out as expeditiously as possible. I certainly commiserate with this–long weekday hours and a desire for a bit of fun on the weekends pretty much preempts poking around in a department store for three hours on the hunt for a new sweater. That’s not to say it’s not enjoyable for some guys, but those are not the ones to whom these services are tailored.

Bernie Yoo, co-founder of Bombfell, created his company specifically because it reflected the way he wanted to shop; namely, he didn’t. “Retail both online and offline is geared toward women,” he says. “And guys are just shoehorned into that same model.” Noting this, he decided to “start it all over” to build his own retail model for guys. “No one has gotten everyday guys to buy clothes more than once a year,” he says. With a monthly package arriving on the doorstep, Bombfell is attempting to change this.

Trunk Club is run by a similarly enterprising CEO, Brian Spaly, who brought his fashion expertise from Bonobos, the trouser company he founded in 2007. For him, Trunk Club is a natural extension of the online marketplace, making it easier for guys to get “really cool clothes,” as he puts it, without “the process of hunting for stuff.” He describes Trunk Club’s mission as “fun” and “delightful,” speaking about his business as if he were a doctor, not a businessman. “Our primary focus is to instill confidence in men. We offer elegance, variety and assortment.”

But neither service pretends to get it all right. Both offer free return shipping if you don’t like what they’ve chosen, and both are making immense strides to better tailor their choices. Yoo told me that when I signed up for Bombfell, the company pulled in all of my publicly available online data to gauge where I lived and what I did for a living to better assist their stylists in picking what I’d like. They even grabbed some public photos of me tied to my social-media accounts to see what my typical style is. An invasion of privacy for some, but for me, I appreciated the effort in trying to capture my style without having met me. After all, it’s what a salesperson would do at a retail store–which is one of the most troubling parts for male shoppers. In the UPenn study, marketing professor Stephen J. Hoch noted that many men would rather “deal with an ATM machine than a sales associate.

If you’re dubious that your taste preferences can be determined by a complete stranger or even a computer, there was a distinct human touch with Trunk Club. Lisa and I delved into my taste preferences in an hour-long phone call on a Wednesday afternoon. Trunk Club understands that most guys don’t think critically about their wardrobe choices, so fortunately the call was less “Do you like paisley?” and more “What do you do on the weekends?” This enabled Lisa, my so-called personal stylist, to determine what styles of clothing I would need without me having to know.

I feared a bit that I was being too vague with my explanations and would end up with a box full of rampant patterns and styles. Maybe I should just head to the mall and dig around for a few hours. But to that end, Spaly waxed poetic: “The theory of choice is overwhelmed by the delight of surprise and serendipity.”

Within a week, I was staring at a hulking box that only affirmed the industrial-era inspiration behind the company’s name. It measured about 3 feet by 2 feet and weighed around 30 pounds. Indeed, I feel a bit bad for the FedEx guy who had to truck this thing forth. The most major drawback: knowing that I’d never be able to afford every one of the heavenly items contained within. My box cost more than $4600 all together (an anomaly for the company, to be sure). Fortunately, I wasn’t expected to keep even half of it. As for the pair of jeans, sweater and dress shirts that I did decide to keep, I simply paid the retail price for listed on the tag. Trunk Club makes their profit from purchasing their clothes wholesale and sells at retail price–the one you’d be paying in Saks or Bloomingdales anyway–so there’s no real price difference.

Did they do better than I could have myself? It’s hard to tell. Mainly because I can’t actually muster the desire to go shopping. But if this experience has taught me anything, it’s that new clothes are shockingly empowering. “We’re not Mother Theresa; we’re not saving the world,” Spaly admits. “But it’s a force for good in the world making people more stylish.”

Turns out maybe I do know something about fashion after all, at least enough to explain to someone else what I like. Sure, it feels like a bit of a cop-out having someone else choose my wardrobe for me. But after the boxes are safely out of view in the recycling bin and I’m wearing these expertly curated outfits, feeling like a veritable fashionista, the rest of the world is none the wiser.

By Nick Carbone, Jan. 28, 2013
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