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Recently, at a bar in Manhattan I made conversation with someone who worked at a startup called Trunk Club. Trunk Club, as it was explained to me, is a company that connects men to a personal female stylist, who then, upon speaking with you, will go online shopping while you are at your presumably well-paying, procrastination-free job. This particular exchange of money for service was quite shocking to me.

I proceeded to ask what can only be described as an over-eager amount of questions. First, and most importantly, who is the target?

“Any guys that don’t like to shop, don’t have time to shop, or that just don’t know how to put things together,” I was told, or rather scolded. I had asked facetiously, with a good picture of the target already in my mind. 25-35 year-old single dudes with disposable incomes and a lack of personal taste. Horrible people.

Trunk Club founder Brian Spaly has a history of helping guys look like they know what they are doing — he also co-founded Bonobos. And like Bonobos, Trunk Club has partnered with Nordstrom, but this time for much more. In July, it was reported that Nordstrom would acquire Trunk Club for a reported $350 million. It’s easy to see the appeal. Dudes who don’t like shopping hand off the task to a (cute, female) expert and in a few days the clothes are at your door ready for you to try on. If it works, great. If not, just send it back. Returning is easy. Plus, subscription boxes are very in right now.

With the emergence of menswear as “the next big thing” in fashion, Trunk Club has perhaps found the great market inefficiency in shopping for single guys who don’t like shopping. In a way, Trunk Club is an anti-fashion start-up. Maybe I asked the wrong question. Is Trunk Club for guys who just don’t want to go shopping but still look good, or for guys who simply don’t know what to wear? I’m sure the employee I met at a bar would have told me both, or neither.

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I wrote previously about the “renaissance man” and how fashion and beauty brands are courting the “real” men. The idea that caring and curating your own look is now cool is a radical departure from the “t-shirt and jeans” approach of the 90’s and early aughts (think Brett Favre in a sturdy pair of Wranglers). The Trunk Club model splits the difference, allowing men to dress well without ever putting much thought into it. That may be over-simplifying, however. Dressing “well” is subjective. Very subjective. A lot of what has made menswear appealing in its current form is the idea that we are all curators of our own style. Your person: a new blank canvas each day, etc. My Trunk Club employee acquaintance would not admit that the service is probably for people whose personal taste is not good enough to paint the canvas on their own. Instead, she noted, “it’s a way to be introduced to new styles in order to perfect your look.”

This idea aligns nicely with the way Trunk Club is marketed. The website isn’t full of guys who look like they wouldn’t know what to wear without an expert stylist shipping them personalized trunks of clothing. It features well put-together, late 20s dudes who simply don’t have the time to find the right J. Crew belt. If it weren’t for the well paying job and full social iCal tab, he would be able to curate his own Banana Republic-inspired look.

The site features some sample trunks with quotes from that trunk’s stylist. Take a look at what Christina has to say about her client, Loren.

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Loren doesn’t have a well-defined, sort of edgy style. Loren hired you because he didn’t know how to dress well. It makes sense for Christina not to admit that. Brands won’t call their clients uncool, or tasteless, even if that’s what their business model is built to take advantage of. Would Trunk Club be willing to admit that they use the service to supplement for their lack of personal taste? I don’t know. Unlike Naturebox, I would expect this is not the kind of subscription box you post about on Instagram.

For me, discovery is at the heart of the problem with Trunk Club. Allowing yourself to be taken out of the decision making process for something that feels so tied to personality and general aesthetic feels so wrong, so farcical. Of course, as I type this, I am wearing clothes that were marketed toward me by companies and corporations big and small—influenced by celebrities and people I saw passing by me on the street. I suppose the way I reconcile this is that my own style is a hodgepodge of different influences and not one bulk order sent directly to my door, as chosen by someone I have never met face to face. That’s a small difference in the grand scheme of things, but it feels much bigger.