I started with a brown fake-leather cross-body purse. It is still my first choice most of the time. However, I have been informed by my stylist (i.e. my wife) that it is a summer purse, and I should be using a winter purse right now. My winter purse is a dark wine-red nylon cross-body.
I also have a larger black nylon purse that is great as a backup, or if I plan to carry some cargo, like gloves or a scarf. And I have a dressy black knitted purse for going to the theatre.
I only have cross-body style purses. I refuse to carry something that I have to clutch onto all the time. And all my purses are what my wife considers small. Even the "larger" black one is small compared to the Queen Mary that she carries around. The dressy one has room for wallet, cell phone, reading glasses, lipstick and tissues. The others can hold all that plus change purse, pen, compact mirror, and pocket knife.