I can't be bothered to change everyday, but do make an effort to change every 3 or 4 days. Just to liven things up. And to bring my babies out of the closet and let them see daylight once in a while. Also weather dictates what sort of bags I carry.
Evening bags get more attention of course. That's about it.
I find it's easier to compartmentalise your bags for easier "changing". For eg. divide your bags into:
1. work handbags
2. work totes
3. shopping/handsfree/casual bags
4. shopping totes
5. evening formal
6. evening casual
7. beach/sports/gym bags
8. high school reunion show-off bags
9. no-need-to-think, matches anything-everything bag
Those are just suggestions...you can refine the list depending on your own lifestyle, and then work from there. It's then easier to change handbags per the occasion and then depending on what you are wearing, go from there. Works for me.