A podcast that I listen to discussed this question:
Do you prefer to be overdressed or underdressed?
Not surprising to many, I always prefer to be underdressed (even ahead of appropriately dressed), for three reasons:
1. It’s always more comfortable to be underdressed (at least for me), and as a human being and a grown man, I have a right to value personal comfort over the judgmental eye of others.
2. Being underdressed is a more approximate physical reflection of the person I am. By nature, I tend to be a person who rejects tradition and challenges norms, and in almost all things, I tend to lean toward the disentanglement and destruction of staid society.
I am the teacher who would prefer that his students call him by his first name.
I am the person who thinks that a verbal thank you mitigates the need for a formal thank you note.
I am the writer who tends to avoid profanity in his work but thinks the restrictions on profanity in television are ridiculous and unnecessary.
Being perpetually underdressed is just another way that I lean away from tradition and societal expectations.
3. It is exceedingly rare that someone cares if you are underdressed.
Case in point: I attended a wedding last week of a friend. I wore pants, a shirt and a blazer. No tie, of course, because I ceased wearing ties years ago. I was aware that I would almost certainly be in the minority in this regard, and I knew that my wife thought I would look better with a tie, but I simply cannot strap that noose to my neck any longer.
Surprisingly, it turns out that I was the only man at this fairly large wedding not wearing a tie.
Did anyone notice this except me? I don’t think so.
Did anyone care? Certainly not.
In the unlikely event that someone did notice or care, do they even remember the absence of my tie two weeks later? Not likely.
In fact, I have found that when I dress more formally than my instincts tell me that I should, there is almost always someone dressed similarly to the way I would have preferred.
Years ago I attended an engagement party at a country club, and after some cajoling on my wife’s part, I agreed to wear a suit despite the heat of the day. It turned out that the only two people wearing a suit were my father-in-law and me. We were both sweaty and uncomfortable for the duration of the affair.
At a recent family gathering, my wife asked me to replace the tee-shirt that I planned on wearing with a sweater or buttoned-down shirt. She almost never asks me to change something I’m wearing (a credit to her), and in truth, I thought it was probably a good idea, too. But when I arrived at the party, I found the host wearing not only a tee-shirt but sweat pants as well. It turned out that my original plans for jeans and a tee-shirt would have been fine.
This is not to say that underdressed is the right answer to this question. I know a guy whose wife teases him because he spends his evenings at home dressed in a button-down shirt, sweater and dress pants at all times. For reasons that I don’t understand but respect, he prefers a more formal look to tee-shirts and jeans, even while relaxing.
The right answer to “Overdressed or underdressed?” is not what everyone expects you to wear. The right answer is what you want to wear.