During spring, winter wear goes to totes in the shed, and summer wear goes to the house. During autumn, summer wear goes to totes in the shed, and winter wear goes to the house. As for organization, there is "going out" stuff, and "working around the yard" stuff.
As I get older, some stuff don't look right on me anymore, and that's when I toss it or donate it. Then, I go shopping for something age-appropriate. I do this about every other year.