I’m a pretty casual guy. Not because I have some deep philosophy of clothing. Just because it usually suits my needs best.
My friend Jeff Tucker recently made the case to me for more formal style. I didn’t agree with his case, but I didn’t disagree with it either. I’m pretty agnostic on this stuff.
To me the way you dress is one of many social games. You can choose to play the game, defy the game, opt out of the game, or fight to change the game. Most of the time I play or opt out, with rare moments of playful semi-defiance (I sometimes joke that it’s fun to be the second most under-dressed person at a banquet, but never the first). I have no interest in trying to change the game with regard to dress norms and expectation.
I don’t care how others dress and I’m not interested in starting a movement. (I dislike movements in general, except the ones I get after morning coffee. Too far? Sorry, couldn’t help myself.) If the cost of dressing down is too high and interferes with my other goals, I’ll dress up. If not, I’ll wear what I’m most comfortable in, usually a T-shirt and jeans.
I spent many years early in my career wearing a suit every day, and many more wearing business casual. Now I hardly have occasion for either and it feels great. I like a nice T-shirt and feel more fresh, confident, and classy in one that fits well with some jeans and sandals than anything else. But I wear appropriate attire to funerals, weddings, and meetings or other events that would be too disrupted if I wore jorts. (Sadly, I got rid of my jorts when they fell to pieces and my wife has seen fit to prevent me replacing them.)
I’m not going to fight for some set of values in clothing, because I don’t have one myself. I try to have as few values as possible. I have deeply held philosophies on the things core to my being and will never compromise without a change in that philosophy based on reason. But the fewer those things, the better. The more things about which I don’t have to pretend to have a position, the better. Clothing is one.