If you NEED all of that spoken out loud, I think maybe I'd separate the different opinions with something other than line breaks, and add more beats. It seems clearer, to me, if it's:
“So what are you going wear tonight?” Just one more thing for me to worry about. Wardrobe, PLUS a propensity to think out loud. Oh well, the thinking out loud works for me; it's the wardrobe that's bringing me down. What the hell do I want to wear?
“How about an old blanket?” It would cover the rolls of flab I just found sprouting out of my back. “Nah, you only have the military ones unless you want to use that new one you got.”
And I need to actually find something to wear, not just amuse myself. “Get serious. I wish I had thought to ask him where we were going, then I’d have some idea what to wear.” I open the closet door and peer inside. “Oooh, I know! Wear the black skirt and the long sleeve white blouse. Skirt’ll be long enough that he would really have to work to get off and if you go somewhere where it’s cold, then the skirt and blouse will keep you warm.” This sounds like the beginnings of a plan. Except, “Yeah, but what if he takes me somewhere where the skirt and blouse will make me look dumber than dumb?”
I don't know, maybe I rescind that suggestion. It still feels pretty weird. I talk to myself, but I don't have huge conversations like that...