Count me in as one of those people who enjoys the more or less twice-yearly chore of switching out my warm weather and cold weather wardrobe. A lot of my off-season clothes are easily accessible, since they're hanging on a rack in the basement, but others are boxed away. (Most woolens go in a cedar trunk that serves as a coffee table in my living room.) The switch-out is a good time for me to do discards, and like most people I tend to discard from among the stuff that's coming into season, probably because it seems natural to try it on at that point.
And actually it used to be more of a chore in the sense of something I didn't look forward to, but now--since I've lost weight and gotten much more into clothes and putting together outfits in the last year and a half--it's a positive treat. Oh, right, I got those tall black boots at the end of last winter! I forgot about those silk skirts!