Familiarity Breeds Comfort

I wish I could tell you there isn’t an adjustment to wearing better clothing but there is. Even a button-up shirt and slim pants are going to fit and feel differently than your XL T-shirt and cargo shorts. A suit is going to feel even more unusual and uncomfortable for a while. But I promise you that the more you wear nicer clothing, the more comfortable you will be in it.

I had a job interview yesterday and had to take the motorcycle because my wife needed the car on the other side of the valley. Not a big deal since I take the bike to work every day that I can, but she died on me as I was on my way home. I got off to see if I could diagnose the problem, tried kickstarting her a couple of times, and eventually pushed her about a quarter of a mile into a golf course parking lot that would let me keep her there for a few hours until I could come back.

As I was sitting in the parking lot, trying to diagnose the problem, and waiting for a ride, I had four guys on a golf cart ride past me and start heckling me about being in a suit getting my hands dirty with a vintage motorcycle. It was the first time since I left the interview that I realized I was even wearing one and how odd it must have looked to anyone who saw me trying to fix my own motorcycle. But I’ve worn a suit almost every day for the past nine years. I’ve full-on sprinted to catch buses and hung out in Toronto laundromats in a suit. I’ve been West-Coast swing dancing and even a session at the skate park in a suit. It’s easy for me to forget I’m wearing one because I’ve gotten so used to.

Now few of those are expected situations and not all of you will get to where you’re that comfortable in something as dressed up as a suit. The point is that the discomfort of wearing better clothes won’t last and – sooner than you think – you won’t even think about what you’re wearing except for how good it makes you look.