For the better part of 10 years of school, most of the shirts I wore had a number on them. The ones that didn’t were mostly generic team shirts from my favorite teams from all sports. I couldn’t have cared less about fashion trends. Somewhere in my 10th grade year, though, that began to change. I’m sure my burgeoning attraction to the opposite sex had everything to do with my fashion epiphany.

For many in my generation (Class of ’84-ish), the clothing status symbol of choice was the Izod shirt. The Polo had not yet gathered enough momentum—at least in Star, Mississippi—to supplant it yet. I eventually owned a light brown Izod, but I must confess that the shirt...

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