For the rest of your life, would you rather be chronically overdressed or underdressed?
For the first six years of my teaching career, I taught at Wootton High School in Rockville, Maryland. It was there I came across a boy named Mack Hollins. I taught his older brother Brian in my AP Lit class, but I can't say I knew Mack well. Mostly, I noticed him for two reasons: 1) he looked a lot like his brother, and 2) he wore a suit and tie to school every day and carried his papers in a briefcase. The attire was especially unusual for a public school, where a t-shirt and jeans were generally par for the course. Maybe he started his tradition ironically, but to see that kind of a joke through for all of high school takes some serious commitment. If I had to guess, he wore a suit because it helped him to take school seriously. It helped him to differentiate himself from the other 2500 odd kids at his school. And I imagine he was confident enough not to let anyone's smartass comments bother him.
It helped that he was good at football. A few years later, when he was drafted by the Philadelphia Eagles, scouting reports noted his sartorial habits as kind of a charming quirk, and evidence of good character. Apparently, he's also handy with a Rubik's Cube, though I don't remember seeing him with one at Wootton.
It's impossible to imagine Mack having had the same success had he been perpetually underdressed, rather than overdressed. Whether fairly or not, he would doubtless have been seen as a slacker, someone with a questionable work ethic and maybe a problem with authority. It's probably not impossible to succeed while being chronically underdressed, but it has to be a lot more difficult.
If you show up to every event in a three-piece suit, you risk being subject to mockery and confused reactions, but people may assume you are an overachiever. If you show up dressed like a bum, people will assume you are one. I'd rather be overdressed. It seemed to work well for Mack.
