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I'm perturbed. Here I am, monitoring the heartbeat of the insurance world, yet a major industry-changing event takes place, and I am the very last to know. Who didn't send me the memo? I could have helped avoid this catastrophe if only I'd been told. I refer, of course, to the adoption of the checked shirt as office wear by every man in the industry.

You probably already know that, in an office environment, the checked shirt is a gigantic sartorial gaffe. Not as bad as wearing brown shoes with a blue suit, or brown shoes with any kind of suit, actually. Not even as bad as wearing a belt with a suit. But still very bad. I'll tell you why.

Here are a few more rules that will help. A T-shirt is not an outer garment. Running shoes are not shoes. Golf shirts are not shirts. Jeans were cool only briefly, in the late 1950s. Your parents wear jeans. Your children wear jeans. You shouldn't wear jeans. Only circus performers and pop tarts sport visible tattoos. There are no more Mohicans, I read somewhere, so there is no room in the C-suite for a Mohawk haircut.

Don't wear a striped shirt with a striped suit. In fact, never wear a striped shirt. Leave that to umpires and prisoners. That way, you will never achieve the trifecta of tomfoolery: the striped shirt with a striped tie, under a striped suit. If you must dress like that, at least complete the ensemble with a striped hat.

How do I know all this? Two reasons. One: innate breeding. Two: I have made every possible mistake in the book. Most of them in Chicago, where I learned that only clowns wear polka dots, apparently. Two other examples come to mind.

The first time I worked on a weekend in the Windy City, I wore what a gentleman wears on such occasions, a blazer, white pants and an open-necked white shirt. To this day, I don't respond well to boating jokes.

The other story involves Donald Rumsfeld, the secretary of defense. I worked for him 25 years ago, and one day he stepped into an elevator in which I was the only other passenger.

I had on an unutterably sharp Mississippi riverboat gambler's suit, with an electric green tie. As the elevator took off, Rumsfeld stared dead ahead at the door, and then turned to look at my feet. From there, he worked his way north. It probably only took a few seconds, but it felt like a lifetime to me, because I knew that sooner or later, our eyes would meet.

Suddenly, the suit I had been so proud of became a serious liability. Did I mention it was orange? Did I mention that this was the most conservative company in the most conservative corner of the most conservative country in the history of conservative behavior?

Our eyes met. "How are you?" asked the man who held my career in the palm of his hand. Completely nonplussed, I could only gargle: "Uhhhh . . . uhhhh." I got off at the next floor.

Buy a white shirt and get used to it. Use the checked shirt to wash the car. You'll thank me.

ROGER CROMBIE is a columnist for Risk & Insurance®. He also covers issues on alternative risk.

July 1, 2006

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