Illustration by Jason Raich

See that horrible couple over there, arguing in the men’s department? Ignore them. She’s holding a dress shirt to his chest, asking him to try it on—and the same one in a smaller size, just in case—plus these other four shirts, five pants, and, oh, do you need a belt? He’s saying he doesn’t need that shirt—it looks itchy—and the Bears game starts in 20 minutes. She’s throwing up her hands, saying never again, and that’s the first thing they’ve agreed on all afternoon.

I know the world doesn’t want to see my 1996 Chicago Bulls NBA Champions T-shirt anymore, but I would rather get a neck boil lanced by Silvio Berlusconi than go shopping at the outlet mall again with my spouse. The idea had been proposed, and a sartorial clash was looming when my well-dressed neighbor Peter told me about Trunk Club, a national start-up that operates from a loft on West Superior Street. Its business model is simple: A style consultant handpicks upscale garments for a client, ships him a box of clothes, lets him keep what he wants, and arranges it so he can send the rest back without charge. The company profits by buying wholesale and selling at retail. The client profits by avoiding shopping.



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I called a Trunk Club consultant named Genna Kashian, who attempted to lure me to the 7,000-square-foot “club” to try on clothes with promises of cold beer and leather couches. I told her I did not want to leave my bedroom, and my free consultation began. How would you describe your style? College T-shirts and cargo shorts. What colors do you wear? Blue, brown, and stained. What are your sizes? I better ask my wife. What do you need? To not be snickered at by the hostess at Gilt Bar.

While Genna searched for the new me in the Trunk Club’s on-site storeroom, I caught up on Friday Night Lights episodes. Two days later, my “trunk” (actually a sturdy FedEx box) arrived, with $1,296 worth of John Varvatos, Jack Spade, Jeremy Argyle, and other guys who sound like they crewed at Yale. The shirts featured colors I’d seen only in Tim Burton films. The chinos were softer than Liberace’s pajamas. A spreadsheet from Genna explained why she chose each item, what to wear it with, and how to care for it. Other than a lavender polo, I wanted it all. Done.

But when my family demanded to see these fancy new duds that had no dog hair on them—and my wife saw the prices—my plan threatened to unravel. I was forced to model each item, and no one could agree on anything. Those Tailor Vintage walking shorts ($78) I loved? My wife insisted we could get the same look for half the price. The comfy green-checked shirt by Scott James ($95)? “You look like half-man, half-tablecloth,” said my six-year-old daughter.

I had to try on everything again for my Skype date with Genna, an arrangement that had its own issues, including, but not limited to, pointing a laptop camera at my crotch for a complete stranger. Halfway through the fashion show, which strangely was kind of fun, I finally understood my problem with shopping. It had nothing to do with my wife or even stores. It was the clothes I’d been wearing. For the first time, I was sporting threads that looked and felt good.

In the end, I kept three items: a Scott James aqua plaid shirt ($95), a Jeremy Argyle fitted dress shirt ($148), and Genetic Denim straight leg jeans ($198). “The guys love these jeans because they feel like a pair of sweats,” Genna said. I plan to wear them to the office all fall. If my wife lets me, I may wear them to bed.


Illustration: Jason Raish