There are those who say that you learn everything you need to know in kindergarten, and that might be where my struggles with fashion first arose. I wore a uniform to my Catholic kindergarten, and, ever since, I have lacked the ability to dress myself with a shred of fashion sense.
And that's how it came to be that I found myself wearing a quality silk tie, a white shirt with cufflinks and a good pair of gray pants, sitting in the bar area of a bowling alley in Kimberling City, Missouri, chatting with a comfortable alum wearing a "Redneck Yacht Club" T-shirt. Which reminds me of the time I showed up at a donor's office in Oklahoma City wearing a polo shirt amongst starched collars and expensive ties.
Usually, I aim to be just a tiny bit more formal than I need to be. If the prospect is wearing a T-shirt, I want to be in a nice polo. If the donor is wearing a polo, I want to be in a nice sports shirt. If the prospect is wearing a sports shirt, I want to wear a tie.
Once the sartorial arms race reaches the suit level, though, I content myself with getting by. Whether the donor is wearing $119 Sears special or a $2000 Italian suit, I'm going with my regular Jos. A. Bank sales suit. And if I need to wear a tux, I start updating my resume.
Obligatory Tangentially Related Joke: Three businessmen on a plane. First guy says, "That suit looks great on you. You must be a Harvard man." Second guy says, "Yes, thank you. I did go to Harvard. And with that classy briefcase, I would guess that you went to Yale." First guy says, "Yes, I am a Yale man." They both look at the third guy, and they say, "You must have gone to KU." Third guy says, "Why yes, I did. How could you tell?" "We saw your class ring when you picked your nose."
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