I only started carrying a purse after I had kids in my late 20s. My current purse is somewhat large, I guess. Nothing compared to what I see in the stores. The only rule (I buy a new one every year or so) is that it must be big enough to comfortably fit my 505.
I am not really into purses or shoes at all. I use them, and therefore I must buy them, and I'm actually pretty picky about them (the plainer the better).
Considering I spent most of my formative years a tomboy to the (almost) highest degree, I've come a long way towards exploring my femininity. I even wear a necklace now and again, and occasionally a spot of makeup as well.