I'm never at ease about my choices about what I wear. I get up in the morning and chose from a fairly narrow selection of "work clothes", pausing a bit to consider if who I might be meeting with that day and what the weather will like. Most of the time I'm only working with co-workers and most of the time it's warm or hot here, so the choice is usually khakis, a short sleeve shirt, and dress shoes. I downgrade to a golf shirt, jeans, and sneakers on "Casual Fridays", though to me wearing anything isn't casual enough.
Only very rarely if I'm meeting with a customer's upper management will I wear a tie and jacket or a full business suit. God I hate that clown outfit! It's literally a middle ages business uniform that looks absolutely ridiculous. Ties? What the heck! They're hideously uncomfortable around one's neck and what's with the vertical stripe of color down a light colored shirt, deep V'ed in by a thin and otherwise useless jacket? How uncool is that? All this so everyone knows what to look like in front of each other, even if everyone looks pretty silly.
The lab I work in makes everyone wear the same blue smocks to protect against electrostatic discharges. Worn over anything, everyone looks just about the same wearing them, creating an inadvertent "work uniform". In a way, it's a relief. Police officers, nurses, and many other professionals and blue collar workers wear uniforms to people identify them with their profession. At least they don't have to think much or care what we're wearing to work, and I don't have to care much if I'm going to be in the lab all day.
Then there's the trap of what to wear when going out with friends or to social events. How dress up is it? What are other people wearing? My wife's fashion sense is even worse then mine. Not that she doesn't dress well herself, but she often underestimates how dressed up I should be.
I shouldn't care, but I'm still very conditioned to care. And maybe that's a big reason I like being naked whenever I can be. It's the uniform God issued us. That's what people look like. That's me. I'm more than happy for other people to look like themselves instead of being weirdly decorated. It's a tremendous relief not to have to care anymore when I and others are nude.