Chucks And Why I Agonize Over What To Wear To Work

My brief and wondrous stint with unemployment ends tomorrow. I will miss midday workouts, leisurely weekday breakfasts with Husband, and voracious pleasure reading. In preparation for my first full-time office job, I’ve spent the last few weeks looking for business and business casual attire. I spent an entire afternoon before the holidays agonizing over briefcases and bags. I found a man’s bag I liked and wondered out loud whether it would look strange in the office. Husband was taken aback because I never wonder about things like that. I mean, if I prefer a man’s shirt to a woman’s shirt, I’ll buy it and wear it, with no questions or worries. To explain my hesitation, I reminded him of a small incident from last summer, when I interned at the same firm I am starting at tomorrow.

My commute last summer involved a bit of a walk and, like many other Chicagoans who work downtown, I usually wore sneakers in the morning and changed into heels at work. Because I’m not crazy. I was partial to my olive-green Chuck Taylor All-Stars, because they are cooler, better-smelling, and easier to slip into my bag than larger athletic shoes. One morning I was running a bit late and forgot to make the shoe switch in my office before heading down to the main conference room for a meeting. It wasn’t a big deal: there were no partners or clients present, just a bunch of interns gathered for a legal writing refresher course or some such nonsense. After the meeting, I took the elevator back up to my office and, as I exited, I heard someone on the elevator snort incredulously, “Was she wearing converse?” As the doors closed, the three people left all started laughing.

Huh. Yeah, forgetting to change your shoes is silly and amusing. But does it really warrant an elevator full of derisive cackling? From my peers, no less? From men, who for some reason I assumed were less catty about these things? Apparently.

That moment didn’t teach me not to wear my chucks to work. I already knew that. It did teach me that I am clueless about corporate life and that small mistakes can be a big deal. I can’t stop myself from making mistakes, but I can play it safe. So the clothes I bought this week are super basic. Black, gray, blue, black, gray, and so on ad infinitum. And the briefcase? I ended up finding a woman’s bag that I liked, but I bought it in bright orange.

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3 Responses to Chucks And Why I Agonize Over What To Wear To Work

  1. Pingback: The Hidden Dangers Of Comfortable Shoes | Bending the Rules

  2. Melanie Carbine says:

    Awesome. I think it’d be great to sneak around to several legal firms dressed in a suit with outrageously colored chucks on. Plus, those multiple pairs of chucks that I want to buy will be a “professional” cost.

  3. Pingback: Fashion Versus Style | Bending the Rules

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