What a great thread, Shannon!
I plan, or not, depending on the day and occasion. Most days I figure it out on the spot. But I'll plan travel capsules, and special events. The thing is, in my life, a lunch date counts as a "special" event, LOL! So the definition is a loose one. If I'm planning in advance, though, I try to come up with options for different weather conditions because nothing is worse than getting all set with an idea only to realize that it won't work with the coat you'll need to wear or your footwear.
When you don't have many clothes in the closet it is pretty easy to pull outfits together on the spot. They may be the same outfits you wore a week ago, but that's what there is.
I have really enjoyed our inspiration threads because they've helped me see another way to manage things and that has been really fun.