My favorite summer dress code: Office Inappropriate

To celebrate the close of summer, I thought I would post an ode to my favorite form of summer dress: Office Inappropriate.

As the warm weather leaves us, jackets replace tank tops, real shoes replace flip-flops, and conservatism replaces poor judgment. Which is too bad, right? Because what fun is conservatism?!

This summer, some of my greatest personal enjoyment came when I could steal down to one of the restaurants in my building–or better yet, one on Michigan Avenue with outdoor seating–or, best of all, the coffee shop at the Merchandise Mart–and work on my laptop–in sunglasses–and marvel at what people felt emboldened to wear to work that day.

I’m not sure how best to describe the things that I saw… not all of it would sound sensational, as I think it was as much the quantity of poor clothing judgment as it was the audacity of any one outfit that caught my attention. (Though I must admit, some of the outfits were head-turningly spectacular, from a faux pas perspective.) Some ideas defied logic altogether. For instance, Recently-thawed-from-cryogenic-hibernation-70’s-guy with his shirt unbuttoned three buttons down the front, with his white suit and white shoes, would have stood out even at a Las Vegas nightclub. And decade-mixmaster-chic with her Uggs, legwarmers, shorts, and blouse, couldn’t be excused for her outfit even if it was laundry day.

Descriptions of my all time favorites defy the imagination; had I not seen them myself, I am certain I would not have believed anyone would have actually worn these outfits. Khaki pants with tiny, green tennis rackets embroidered all over them? Four inch high, fire-engine red stilettos with an unremarkable gray suit? Washed cargo pants with a blazer? Sheer tops with purple bras? Skin tight shirts over beer bellies? Skimpy, black undergarments beneath white linen pants? An orange-tipped faux hawk with a tie? Printed t-shirts which, once I could decipher the lettering, left me wondering about the audacity or the ignorance of the wearer?

This was the stuff of over-the-top sitcoms. Yet there it was, in the real world… where I could witness it, marvel at it, and most of all, enjoy it. These were people grabbing life by the horns! They were standing up to The Man! They were taking risks! (More than they probably knew!) I’d suggest that the rule for appropriate work dress is that if you have any question at all when you’re putting it on, then you should likely skip it, but from the way most people carried themselves, it’s not clear to me that this advice would do anyone any good. Most of the people I saw looked like they had put themselves together precisely how they wanted to be. Which is fine by me. Like I said, what fun is it if everyone’s dressed conservatively and appropriately? What would I write about then, guys whose belts don’t match their shoes?

For the record, I did notice more women making Office Inappropriate fashion statements than men. Also for the record, I believe that the discrepancy was more a matter of available options than anything else. Had Dolce & Gabbana offered men more than just white loafers and oversized white sunglasses, I’m certain the OI male trendsetters would have put those other items to use, too.

Alas, ‘tis now fall, and so goes my summer fun as the weather turns, the outdoor cafes close, and the people cover up. I guess that’s OK. At least now we’ll maybe get a little work done… unless the forecast for today is right and the temperature will hit the low nineties… in which case, I need to dig out my sunglasses and find a place to park myself for lunch!

Jason Seiden is Co-founder and CEO of Ajax Social Media, a training company that shows professionals how use social media to work more effectively.