Call me old fashioned, I always have on jeans/slacks and closed toes shoes, even mid-day in Texas. A throw back to when I ranch worked outside daylight to dark.
Me too and something to wear on top of my bald head except when I'm indoors.
To some extent, I do care about what I wear but I don't really care about what I "look like". I know what I look like. I look like an old, fat, balding man. That's why pretty young waitresses spend time with me because they know I'm harmless and I tip well.
Before I turned 50, I couldn't get the time of day from them. They all presumed I wanted something when all I want is some cheery conversation and to look at a pretty face. An occasional hug is nice too.