Your question made me smile...a lot. I'm a people watcher. Everywhere I go. Whatever I am doing. The ultimate observer. Much like my dog here, Charlie Brown. He's the love of my life. A few years ago, I'm at ATL going between concourses and I have a couple of hours to kill. I'd been comfortably carrying a purse for a number of years by then to the displeasure of quite a few people. I picked up on these observations: There were three types of guys. One type had every pocket crammed with crap, bulging. He looked pretty silly and an uncomfortable way to travel. The second was carrying a laptop case. Now laptop computers are generally two inches thick. However, these cases were almost always closer too twelve inches thick. The guys had nothing in their pockets. Flat. In essence, they had turned their laptop case into a de facto purse. They were indeed carrying a purse, but were too ashamed to admit it. The third of the group also had flat pockets, but was traveling with a female who was carrying a purse. These guys should have just had his own purse because hers was bulging. Anyhow, I found it all amusing.
But to answer your question. I have about four purses, browns, blacks and neutrals. I do need a Spring and a Summer one now. Kind of like shoes I'm finding : you never have enough. In mine I always have a couple of lipsticks, a gloss, a mirror, a hair brush, nail boards, a pen, wallet, lotion, rollerball fragrance, glasses, and tissue. I keep my keys clipped on the outside. It always goes with me. Everywhere I go.