French cuffs and a tie at the Hillbilly Bowl in Kimberling City, Missouri?
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."