Zack’s New Trunk Club Wardrobe

22 Jul


I’ve never dressed well. I’m not being modest, it’s the truth. Growing up in Chicago, my grade and middle school wardrobe was exclusively Bulls t-shirts. In jr. high, I “matured” to funny Seinfeld t-shirts and Miami Dolphins jerseys that I paired with Old Navy cargo jeans. In high school, I expanded to flannel and still wore Old Navy jeans. The last ten years was a loose collection of t-shirts, hoodies and jeans.  I just never spent money on clothes, always preferring to spend my extra cash on festivals, vinyl, concerts. You know, anything but a $150 pair of jeans. 

Caitlin’s been really helpful in making me presentable the last couple years, especially with her suggestion to start shopping at Stag. I resisted at first, but she’s helped me pick out a great pair of jeans and favorite versatile blue shirt and bought me a couple sweaters, my favorite canvas backpack and more for holiday gifts*. We’d been meaning to go back this summer, but we always put going to Barton Springs over going clothes shopping during our too-short weekends together. Then I saw a story about Trunk Club in Mashable, and the service appealed to everything holding me back from doing some serious clothes shopping. I e-mailed Caitlin asking if I was crazy for thinking about doing it and she wrote back, “It’s not crazy at ALL. I LOVE it!!” Caitlin’s a master of getting awesome stuff from ModCloth**, so with her enthusiastic go ahead, I requested my first trunk.

*I adore Stag. Usually it’s not that fun to go clothes shopping for a dude, but Stag has such amazing stuff in there, I drool the second I put my foot through the door. I feel safe knowing that whatever you get from that little boutique, it’s quality and will last a really long time.

**I would not call myself a master. I’m more like an addict who doesn’t have the money to really feed my addiction so I just have a wish list that’s 276 items long, instead.

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I hate trying on clothes at the store. Grabbing 2-3 things and having to either change in a cramped room as Caitlin watches me* or trying the clothes on alone and then doing that awkward half walk out of the dressing room to find her. The worst. The fact that with the Trunk Club, I could avoid going to stores and could send back anything I didn’t want was really appealing. And it was pretty cool getting to talk to a personal stylist. My stylist, Ann, called me and was super friendly and helpful and walked me through the kinds of things I needed. I told her I desperately needed comfortable shoes, somewhere between sneakers and tux shoes for walking around Europe. I needed a couple short sleeve collared shirts. A nice pair of jeans and a nice pair of non-jean pants. And a belt. Three days later, my first trunk arrived on the day we were going to Qui, just in time, since I didn’t own anything I’d feel comfortable wearing there. I was sad Caitlin couldn’t see the clothes with me the second they came, but I was excited to surprise her at the restaurant. 

*This makes the experience sound kind of creepy and uncomfortable. Maybe we need to just start having Zack take selfies and text them to me or something. It’s not that you make me uncomfortable at all. I just get worried that people are thinking things when a guy and girl go into a changing room together and then I feel pressured to like whatever I take in there. And then I don’t want to go back if it doesn’t fit right. Bah. Woah, woah, woah. Relax darling. First of all, the Stag dressing room doors are way too low to give anybody any ideas. Secondly, they’re there to serve us. We ain’t pressured for nothin’.

croppedI loved everything I tried on and easily picked out the first outfit I’d wear out to Qui and The Big Lebowski Quote-a-long Friday night. The shirt (Ben Sherman Laundered Buffalo Gingham ModFt button-down) fit great, the jeans (Fidelity Impala) instantly became the best pair I have, and the (Calypso Suede) shoes are the best pair of I’ve ever owned. I do love those shoes.

IMG_3731This (Jack Spade Woodward Plaid Woven) shirt was almost twice the cost of the previous one, but I really loved the fit, so I kept it*. I was on the fence, but Caitlin insisted. Also, the (PACT Gravel Stripe Crew) socks were a nice touch. The less white socks I have, the better. One thing I forgot to tell Ann I needed was shorts, so we took a trip to Stag anyway to pick up a couple pairs, including this white pair. Caitlin spotted these and picked them out. I wouldn’t have thought to get them, but she’s really good at this stuff.  

*Let’s be honest with the people. I thought he was the most handsome thing to ever walk the earth and insisted he keep the shirt, and he was persuaded.


This was the only shirt I didn’t keep. It’s a fine shirt, but I have a ton of similar long sleeve shirts, so I wasn’t in need of one nearly as badly. Also, Caitlin thought I was crazy for not being as into these pants as she was. She threatened to fight me if I thought about returning them. A simple “you look handsome!” would have sufficed 😉*.

*Sometimes you just gotta use stronger language to get your point across.

I am throwing down one more paragraph here because seriously, people. Let’s talk about those pants. Those pants are the kinds of pants that do the same thing to a lady that Elvis’ hip swing did. Those. pants.

IMG_3736After we took pics of all the clothes, we played around with the color settings on the camera. That’s it for now, but I’ll have to send away for another trunk after I pay off the Europe trip, and/or stop in the Chicago office to try things on in person when I’m home for Thanksgiving. I couldn’t recommend Trunk Club any higher. Thanks Ann. And especially thanks Caitlin for encouraging me, letting me indulge myself with a little fashion show and giving me your honest, expert opinion. I get to pretend to be a stylist, and Zack puts up with it. You gotta love a partner like that.


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