Introducing…the Work Short

It’s well known that I am a trendsetter. A trailblazer, if you will. One who boldly goes where others fear to tread. And while my fashion sense has been charitably described in the past as “disastrous,” I am happy to announce that this summer I have finally done it. I have broken new ground, shifted the paradigm and transformed my revolutionary thoughts into astounding action. And this time I am poised to turn both the fashion world and the work world on their collective ears.

Am I building it up too much? Do you fear that I am overselling this concept? I think not. For I have done nothing less than created an entirely new category of dress.

Today I introduce to you…the work short.

That’s right. I have finally successfully crossed the heretofore forbidden threshold of wearing shorts to the office.

But like all good stories, let us start at the beginning.


Back in the old black and white days, men wore suits everywhere. They sported fancy hats and used garters to hold up their socks. They starched their collars and wouldn’t dream of complaining about the heat. But as the years passed and styles changed, men ditched their hats and traded their three-piece suits in for trousers and sport coats. Garters were reduced to their current status as accessories to the most awkward part of the wedding reception.

By the time I started working in an office the appropriate dress was trousers (aka slacks) with a button-down (or is it called an oxford?) shirt. For big meetings you’d add a tie and a coat. Perhaps even a suit for really big meetings. In the summertime we were theoretically allowed to switch to short-sleeved button-down shirts, but that look is so horrendous that few (outside of the IT group) bothered with it.

Then the Dockers revolution hit and it became acceptable to wear khakis (aka chinos) with a button down shirt. But the big win came in the summer – finally you could replace the button down with a polo (aka golf) shirt. Now, I’m no fan of the golf shirt – it just screams corporate wanker – but it’s certainly a big improvement over the button-down in the heat.

Casual Fridays brought another workplace revolution – jeans on Friday. Now, my friends, we were finally getting somewhere.

So this became the office dress code for many, many years: slacks and a button down shirt for most of the year, khakis with a golf shirt in the summer and sweet, sweet denim on Fridays.

How funny it is to look back and to think that I was satisfied with that arrangement. What a precocious, naïve youth I was.


My first foray into breaking the dress ceiling involved increasing the frequency of jean wearing. For example, if I had Friday off, I’d wear jeans on Thursday because it was “my Friday.” If it snowed I would wear jeans because “It was snowing.” Over time, I dispensed with the excuses altogether and just wore jeans whenever I didn’t have a client meeting.

And then the summer came. Denim, while the single greatest clothing fabric ever invented, does have an unfortunate tendency to get a little sweaty in the heat. I needed a new solution. But there was no way that I was going back to real clothing.

Something had to be done. And I was just the guy to do it. And that something is called: WORK SHORTS.

But there was still a lot of work left to do before my dream would become a reality.


The first thing I realized is that “work shorts” do not exist in the eyes of the fashion world. There is no “work short” section in the store. Most shorts that you encounter are either board shorts, athletic shorts, cargo shorts, or the dreaded jean shorts – none of which qualify as “work shorts.” They’re just not formal enough. And Bermuda shorts don’t work either. A young guy wearing Bermuda shorts runs the very real risk of getting dragged into a pick-up shuffleboard game on the walk to work.

After much searching, I finally discovered there’s a rare type of short that fits the bill: khaki colored, flat-front, mid-thigh length with discreet pockets. I stocked up and breathed a sigh of relief. “Operation: Find Work Shorts” was complete.


I will admit to the fact that I have, upon occasion, worn a tee shirt to work. Unsurprisingly, I have work (fancy) tee shirts and regular tee shirts. Somehow, a work tee shirt with jeans and shoes seems acceptable, especially in the advertising/marketing/promotions world. Yet pairing the “work tee shirt” with the “work shorts” just didn’t cut it. The tee shirt diminished the shorts and it crossed my (already quite low) standards for office attire – it was just way too casual. So I have reluctantly reintroduced the golf shirt to my wardrobe. It’s a small price to pay to pull off shorts in the office, though.


To date, I’m still really not satisfied with my shoe situation. I’ve been wearing Teva sandals with the work short-golf shirt ensemble but there’s something about exposed man-toes that hurts the pseudo-corporate look that I’m going for. I’ve tried the loafers with no-socks look, but it makes me feel like I should be meeting Muffy at the club for lunch. Perhaps I’ll sample some boat shoes. I’m really stumped on this one, so any tips are greatly appreciated.


Take it from one who’s been there and let me give you a small bit of advice if you’re thinking about embracing the work short concept. Unexpected client meetings have the potential to ruin everything that we’ve worked so hard for. It’s probably best if you keep a bag of “Big Boy” clothes in the office for emergency use. This will prevent you from getting into too much trouble with the boss.

You know the more that I think about it, aside from the shoe dilemma, the more I feel like I’m really on to something here. This morning, for example, my wife saw me and said, “You look nice today.” Incredulously, I stammered back, “You mean you like my outfit? The whole work short thing is working for you?” And believe it or not, she did and it was.

Of course, when I later met a friend for lunch (on a 90+ degree day he was wearing a tie and a long-sleeved button-down shirt with his initials on the frenchified cuffs) and he declared upon seeing me: “So now you’re wearing shorts to work you slob? You’re pathetic.” So I guess you can’t win them all.

That’s okay. Trailblazers like me need to possess a thick skin. I’m sure people laughed at Ben Franklin, Thomas Edison and Bill Gates, too. It’s lonely here at the bleeding-edge of office fashion – but believe me it’s well worth it – my calves are cool and comfortable and I no longer have to pretend to be Scottish in order to wear a skirt to work on hot days.


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