My only consideration is my mood. I may wear the same bag for months at a time and then get in a mood where I change every single day. I don't ever "match" to my outfit, but I will change either the bag or the outfit if it outright clashes. My wardrobe is pretty tame (my flair is in my bags!) so I don't run into clashing very often.
I need one of those organizer things! Note to self: Gotta do a search for more info on those when the search feature is back up!
I need one of those organizer things! Note to self: Gotta do a search for more info on those when the search feature is back up!