Probably 4 - 5 times a week usually. I plan what I will wear, and always co-ordinate my shirt/ shoe colour with my bag colour. If I don't have time to switch out a bag, I make sure I grab a shirt that will match what is currently packed.
I have only become fanatical about purses in the last 9 months or so, before I had a huge tote and that was it. I have found that since I have nice purses and change them out, the amount of crap I carry has decreased significantly, when I change my handbag, I throw away junk that has accumulated. Works very well for me.
I wish you well,
Bridget