If your Halloween costume includes a diaper, don't wear it to work

Toward the end of the day on the Friday before Halloween, my office holds an annual costume contest with legit prizes like a weekend up in New Buffalo and tickets to the Bulls. Let me put it this way: There’s an inverse relationship between fabric and winning. It’s all in good fun because even the older people get into it and the men dress as skimpy as the ladies. I’ve been working out a bunch, so here’s what I want to know: sumo wrestler — OK or not OK?

—Mr. Roboto

Sometimes, I wake up in the morning and wonder what it is I’m doing with my life. But then I rub the sleep from my eyes, unhook the hose on my sleep apnea machine, open up my email and am reminded of my life’s mission: to help grown men figure out when it’s OK to wear a diaper.

Let’s do a quick risk-reward analysis. Best-case scenario, your costume goes over well and you score Bulls tickets. I assume that any company where employees seriously consider wearing a sacred Japanese thong during work hours doesn’t make enough money to hand out floor tickets. For argument’s sake, let’s say you get four seats at club level to the Pacers game on Nov. 16. Good seats, good opponent. On Stubhub, those four tickets go for a grand total of $712. Congratulations.

Now let’s examine what happens if things go totally sideways, you’re bad at tying knots, and, after a particularly vigorous bout of Dougie-ing, you get canned. You’re a 25-year-old sales rep. I know this because you managed to fit “legit,” “inverse relationship,” and a reference to your fitness regimen into a single paragraph.

According to Glassdoor, your base salary is probably around $55,000. Now let’s suppose your blemished résumé keeps you from finding comparable work for two months. That means you’re down $11,000. Adding insult to self-inflicted injury, you probably won’t get unemployment benefits because your employer fired you for just cause, and none of that includes the emotional strain and embarrassment you’ll feel. Seems to me like the scales tip toward skipping the sumo wrestler get-up.

Of course, the most likely scenario involves you not winning Bulls tickets, not losing your job, and pictures of you wearing a diaper not going viral. It does involve those photos making the rounds through the stinking mire of social media. “Think about those pictures on Facebook and your clients looking at them all year-round,” adds Rick Maher, who owns Effective HR, an HR consulting firm. “Think about your butt cheeks and the sumo costume.”

And as an ill-fated Brazilian wax once taught me, avoid all situations where strangers are reminding you to think about your butt cheeks.

Is it OK to wear blackface with my Halloween costume?

No.

Have you seen “Mean Girls”? Where they talk about how Halloween is the only night when it’s acceptable to dress like a slut? Even though that movie took place in a high school and is obviously fictional, a lot of people in my office seem to take that sentiment to heart, dressing in very provocative ways for our Halloween office party. I’m in my 40s with a family, so maybe I’m just out of touch, but is it wrong to ask my co-workers to wait until after work to bare their midriffs and put on their garters?

Jessica in Naperville

Since it sounds like you’ve been out of the game for a while, let me get you up to speed. Today’s incarnation of All Hallow’s Eve is the worst thing to happen to young women since I joined Facebook. Here are the four most popular female costume options this year: sexy nurse, sexy cheerleader, sexy Miley Cyrus, and sexy Miley Cyrus in a nurse costume.

Do feel some compassion for your young female colleagues, who are pressured to dress scantily, and then could be crucified if they overdo it just slightly. (The quiet majority of women go for something more cerebral.) Keep in mind that those who do bare their midriffs might not be trying to ruffle feathers, but do the exact opposite — conform to the tacit expectation that they strap on their garters.

There’s a significant generational gap between you and these colleagues, so you’d be wise not to sound like a scold. I’d skip any value judgments and cut to the professional consequences of trying to pull oneself up by the bra straps.

“They need to remember that their appearance is part of their visual resume. They have to dress the part, which includes clothing, hair, makeup, and accessories,” says Brenna Smith, founder of SheNOW, a women’s magazine for the young and the professional. “If you can’t imagine a successful female CEO wearing it, put it back on the hanger.”

No matter whether one sees the rise of the form-fitting costume as a sign of workplace progress or a misguided corruption of feminist ideals, measured and sincere advice from an experienced female colleague should be welcomed.

Till next week.

Got a question about how to act around the water cooler? Tongue planted firmly in cheek, we’ll find an adult to answer it. Email us at advice@chicagogrid.com.

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