January 14, 2016 11:00 PM

What Is It: Trunk Club, service that employs a stylist to pick out your clothes based on your preferences then mails them right to you.

Who Tried It: Alex Apatoff, Senior Style Editor

Why We Did It: I needed a New Year’s wardrobe refresh, but I really hate online shopping. So if someone was willing to do it for me, who was I to argue?

Difficulty Level: A 1/10 for the whole process, but a 4/10 for trying clothes on, because trying clothes on is Le Worst.

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There I was, disclosing my height and weight over the phone to a total stranger, as she repeated it all back to me in a chipper tone. I struggled to answer basic questions about myself (where did I like to shop?) and wondered if it was possible that I’d reached the pinnacle of human laziness by allowing a friendly lady in Chicago to pick out all my clothes for me. But I’m getting ahead of myself.

Trunk Club was initially started as a brick-and-mortar location where guys could go to get style upgrades from knowledgeable shoppers, and I first heard about it when my Chicago-based mom ordered up a trunk for my perpetually giant-suit-wearing dad. She liked it so much that when they expanded into womenswear, she tried it for herself, and then when they expanded to offer the service over the phone nationwide, I tried it for myself.

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You fill out a little survey online, then a stylist (mine was Chelsea) calls you up and asks questions to get an idea of where you shop, what you hate, and so on. A short while later, an email arrives in your inbox displaying about 10 items she’s picked, and you can ask to swap a few before she packs up the trunk and sends it out. In my case, I’d said I was looking for mostly good work basics, a perfect LBD and a few tops outside of my comfort zone; when her picks came through with more jeans than I wanted, I let her know, and with a few quick changes, the box was in the mail.

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Trunk Club takes the “styling” component of their job very seriously, putting together complete outfits with your pieces (as seen above). That way you don’t feel like you’ve assembled a random selection of things you love that don’t go together, which is sort of the motto of my closet. So even though I was skeptical of items like a long vest and turtleneck, I liked the way Chelsea assembled them into multiple outfits and was willing to give everything a try.

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The trunk arrived at my apartment promptly and was very neatly assembled with contemporary brands that can all be found at Nordstrom. We don’t have a Nordstrom in N.Y.C., so I appreciated the selection of their in-house brands, but the rest you could find at any department store (think Equipment, Vince, Kate Spade).

I got to work trying everything on; after all, you have 10 days to return the box, and anything you keep is charged to you, so time is of the essence. I started with the things I knew I wouldn’t like: the vest (hated it, made me look insane), silk track pants (shockingly great, but pricey) and the turtleneck (even more shockingly great). Then I moved on to the easier stuff: the flare jeans (cute, good price, but didn’t need them) and tops (all weirdly boxy and huge, and a total non-fit for my body type).

Finally, I tried the pieces I would have picked out for myself: a luxe cashmere sweater by Equipment (gorgeous, but for $298, way too see-through to consider), some LBDs (all cute and flattering) and a DVF pencil skirt (expensive but absolutely worth the money — it was practically made for me).

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I provided feedback via the app as I tried things on, and while there were some glitches — for instance, marking items as “bought” when I hadn’t yet — I did like that it showed the most recent sale price at Nordstrom. In some cases it was lower than on the price list included in the box, and in other cases it was higher; Trunk Club says they’ll honor the lowest price. And you can also use the app to give immediate feedback to your stylist, either on the whole trunk or piece by piece, so she has a more informed view of your style for the next one.

After much debate, I decided to keep the Vince turtleneck. In the spirit of Trunk Club, I figured I should choose an item that was way out of my comfort zone, but somehow just right for me. I’ve worn it a ton, and loved that Chelsea gave me the tools to try something new and picture how it would work in my wardrobe.

The Verdict: It was really fun to have someone pick things out for me that I was surprised to find I loved; for that alone, it was worth the experiment. The contemporary price points are too high for me to do it on a regular basis, but I can totally see using this service for a special occasion — having someone like Chelsea send me 12 dresses (some safe, some surprising) to try on at home with all my accessories would be a smart and easy way to shop.

Would you use a shopping service like this one?

— Alex Apatoff

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