Why do you dress that way?

I get asked this a lot #

It started in high school. I did stage crew for my high school theater’s productions, and there was a long-standing tradition that all students dressed up the day of opening night for a production to raise awareness. For one production, I wore a suit to school for this purpose, just like maybe fifty other students. The day after, when everyone else had returned to their normal dress, I came back to school in a shirt and tie. And the day after that, and the day after that, and the day after that, for a decade.

Why? #

I think, deep down, just because I liked it. I liked looking nice. In a vain way, I think I was also looking to draw a distinction between myself to my pajama-bottom-wearing classmates. I’m not trying to say that someone wearing pjs to school isn’t smart, just that they’re not going out of their way to impress anyone—and I was.

There were reinforcing factors, too:

• I was told more than once (especially in college) that “this was the way everyone dressed when I was in school.” Occasionally, I’d be compared to someone’s hard-working father. I liked these comparisons; harkening back to a “more civilized age” (which was almost certainly not more civilized, but in my mind it was).
• My dress modified my interactions with people. The police officer at the grocery store no longer asked to see my receipt. I could walk into off-limits areas and no one would question it.

In my own mind, I was bouncing between two visions I was trying to “cargo cult”, essentially:

1. A billionaire playboy, rich and successful; a Tony Stark or Bruce Wayne
2. A brilliant Bell Labs engineer, like Dennis Ritchie (co-creator of UNIX), or one of the inventors of the transistor

The Decline #

My desire to wear the outfit began declining around the same time that my perceptions of much of the world were changing. On the one hand, the tech giants that I had admired—home of several ex-Bell Labs staff—stopped pretending to not be evil. Tech products pivoted from being cool upgrades to our lives to ways corporations could spy on us and squeeze out our last dollar. I started thinking about income inequality in the United States, and the role that billionaire playboys have in that. Through all of my disillusionment, I kept wearing the outfit, at least to work, to distinguish myself and make an impression.

That changed in 2020. In March we were sent home from the office, and in May I was laid off. In lockdown, nobody could see what I was wearing or cared. I took up gardening, woodworking, and other dirty trades that were not amenable to keeping my expensive white shirts clean.

I still wore the shirt and tie from time to time, for work mostly, when I got a new job. I don’t think it has quite the same effect transmitted via camera, though, and I’ve worked remotely ever since the pandemic. As lockdown eased, my friends were shocked if I didn’t wear the shirt and tie when I saw them, so I kept wearing it in part to meet their expectations.

Today #

I only wear the shirt and tie maybe once a week, when my schedule lines up right and I have to be seen on a video call. Bigger picture, though, I think my idea of success has changed. I’m not seeking to jetset around the world anymore, or to make some big technical breakthrough. For me, now, success looks like a good potato harvest and sharing a bottle of bourbon with friends. And that I can do in a t-shirt.