I began the discarding process, and so far I feel pretty good about it. For starters, touching each piece to determine if the item stays or goes works well for me. I was able to let go of a lot and there were really only a few items that gave me pause*. I took out two bags of trash (e.g., clothes too old and frayed to pass on to another person, clothes with stains that I couldn't see when I viewed them in the closet but became embarrassingly clear in the light of day, old wire hangers, etc.), three bags filled with donations (including quite a few never-been-worn pieces), and one box to send to mom with a couple of jackets for her and a few shirts for my niece. My current thought is that I'll buy another set of drawers to add to our closet system so I can put the remaining pieces (sweatshirts, sweaters, and pants) in drawers, freeing up that space for my crafting supplies (which are stored in half of Hen's closet right now). But even with the stuff on the shelves you can see immediately how much nicer it is than the other side where Darren's shirts, sweaters, and pants are. (He's not interested in discarding so the best I can do there is folding and straightening, which will still be an improvement.)
*My favorite sweater of all time, which I'm getting rid of. My wedding dress, which I kept. And my unmentionables from my pre-Henry days, which I'm also keeping.