I've kept a few business oldie shirts and ties (including Mickey Mouse and Jerry Garcia versions) for the wedding and funeral days, plus slacks so that I can quickly respond when Jackie asks me "Oh, you're wearing that?" when a more formal outing has been announced. Otherwise for the last 30 months it's been t-shirts-sweatshirts-shorts-or jeans in some combination with ball cap that corresponds with team logos. One pair of boots for winter shlogging, and "nice shoes" for the more formal days (see above question). Jackets for colder days, hoodies on others. There is Tom's fashion sense. Oh, and sneakers. Not no athletic shoes, running shoes, or trainers, nothing endorsed by any athlete. If they fit, they're fine.
Thoreau was right: Simplify. And when your lesion filled brain is making everything just a little harder, the less you have to concern yourself with on the outside the better.
Clothes get donated to the Salvation Army and the odd bins you see all over that ask for clothes and shoes which are sent off to who knows where by unknown people who may or may not be making profits on it. The local media checks on this stuff on slow days. I just hope that somewhere some child in a Third or Fourth World country is wearing my Saturday Night Fever t-shirt with the upside down logo.
Stuff, like people, TV shows, and poorly maintained cars come and go in your life all the time. Some things do stay, like my wife, some friends, and autoimmune diseases. I treasure them (not the diseases per se yet they remind me time is short), but there are pieces of clothing I have that I shall try my darndest never to part with: