Can a Stranger Dress You Better Than You Dress Yourself?

Can a Stranger Dress You Better Than You Dress Yourself?

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. 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 & Mule sends accessories only, and Frank & Oak lets you choose exactly what clothing items you’re getting.

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. 

“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.”

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. 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 in the recycling bin and I’m wearing these expertly curated outfits, feeling like a veritable fashionista, the boxes safely, the rest of the world is none the wiser.

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