I avoid carrying a purse whenever possible. So, most of the year I am carrying my essentials in jacket pockets.

I pretty much only carry a purse if I have to be wearing an outfit that does not have sufficient pockets. I have a modest stash of purses/shoulder bags for this purpose, and which one I use depends on how much stuff I need to be carrying. Most of them are neutral/earthtone colors, so they won't clash with what I'm wearing. I'm pretty utilitarian about my bags that way.

In addition to this, I have a couple dressier clutches for the rare dressy occasion. One was an emergency thrift store purchase -- a tiny tan suede thing that goes with everything, and the other was a splurge on an oxblood red Cartier that I saw in Paris, which I would have regretted not buying. Gotta take advantage of duty-free sometime, right?

I'm not worried about my purses going in/out of style. I've never had the energy to follow trends, so I just buy things that I like, that I feel will last a few seasons style-wise.