For most of the riding season, I use a small shoulder bag purse that came with a small zipper wallet that is just big enough to hold essential credit cards, insurance card, and cash. So, I just take that out of my purse and stick it in my jersey pocket. In the early spring and fall I use a bigger purse and wallet, so before a ride, i have a routine: I know I need 3 cards-- license, Blue Cross card, and credit card, along with my cell phone. When I get those out of my wallet, I also take some cash, although i always have 5-10 dollars in my bike bag. I have a wrist road ID that i wear when i am riding alone or with a group. I don't wear it when I ride with my husband or my very close friends who kow how to contact my husband.
There have been a couple of times I've left my license, etc in a jacket pocket, but they have always been during winter sports-- hiking, snow shoeing, or x country skiing when I go throught he same procedure.