What not to wear?

“Feel free to wear jeans – our whole office is jeans-casual during April because of the construction we’re doing in the suite.”

These words of dress-code guidance were shared with me last week by an executive at a client’s office. I recently began work as a consultant, and, despite a recent trend in many workplaces of going casual, there is still something inside of me that makes me not trust that it’s really OK. As a Consultant, they probably expect me to wear professional attire. Like a suit, or at least a jacket and pants. Look the part of the Expert. Yet, the executive’s guidance seemed sincere, and she herself appeared to be leading by example, in jeans and a black long-sleeved shirt.

That one sentence – an unambiguous invitation to dress down - plunged me deep into an inner conflict, dredging up painful memories from my adolescence. I was transported back to an age when kids, above all else, want to fit in. In an attempt to gain access to the Cool Kids, I decided to go out for softball. The only problem was that in my small school, it was already obvious who the Gifted Athletes were, and it was quite clear that the coach had already chosen these girls as his favorites. I caught a fly ball to right field for the third out in the first inning of our first game that season, and rarely saw action after that. And, as if it wasn’t already obvious, it became abundantly clear that my God-given talents and abilities made me a much better fit for musical activities rather than athletic ones.

Nevertheless, my membership on the softball team earned me entry into the big Spring Sports Banquet, where Awards were presented! and Speeches were given! It was a Very Big Deal in our school. I agonized for weeks over what to wear and with whom would I be invited to sit. My dad was going to accompany me, for parents attended, too. After much deliberation, I finally rationalized that it would be better to be casual, because after all, this was a gathering of jocks, and surely they wouldn’t be dressed up.

I don’t remember exactly the outfit I chose to wear, but I do recall with razor-sharp clarity being MORTIFIED (as only a teen can be) upon arriving, a few minutes late, and realizing that I was completely underdressed. All the other girls were wearing dresses! Everyone! Even Becky and Michelle, and Laurie for cryin’ out loud. Holy crap. Instantly, I turned to my dad and hissed through hot tears, “we need to leave. I am not dressed up enough. Let’s go. NOW.”

My dad, bless him, took me home. I don’t remember ever speaking of this incident again. You would think I would have learned a lesson from this scarring incident. But readers? You would be wrong. Because evidently, I am a slow learner. Years later, the summer before college, I botched the dress code again.

This time, my mom and I were attending a reception for incoming freshmen from the area, hosted by local alumni. “You should probably wear a skirt,” said my mom. But, me being Me, what I heard was, “Go casual. Surely no one will be wearing skirts.” And once again? I was way off. The guys were wearing suits (!) and all but one other girl had actually put on skirts. I made a beeline to the other girl with the capris and stuck to her all night. My new BFF.

Twenty-some years later, I still agonize over appropriate dress. “Helpful” instructions confuse me. “Dressier business casual?” Uh, what’s that? “Cocktail attire?” WTH?

So, it was with trepidation this morning that I decided to take the executive at face value. I threw on jeans with a green linen, belted jacket and black boots. And you know what? The jacket made it work. I was among the more dressed in the office.

But when they lift their Casual April dress code? I’m totally wearing a dress. Meanwhile, I may have to call in Stacy and Clinton for an expert consultation on my wardrobe.