I never take my good bags out in bad weather, I usually take my LAMB Lesportsac ones when it's raining or snowing.
I definitely choose my bag based on what the weather is like outside, what I'm wearing, and what I will be doing that day. Patent leather is a wonderful choice for stormy days here. I usually don't worry about my regular leather bags too much. But if I was outside for a prolonged period I would cover them with my coat. I would rather get wet than let my bags get soaked!
I carry the same bag, but pack a plastic bag inside to put my purse in in case of rain. Depending on which shoes I have on, they go in the bag too.
For some reason I get surprised by weather a lot, I'm unprepared so I have done my share of having my head mostly out in the rain but the LV is under the umbrella.....
Today, it is going to rain and thunderstorm. I have to go outside. I'm going to change into a handbag that I don't care about as much if it gets pelted by rain. Does anyone else do the same thing, or do you just use what you have at the moment? After all, it only takes me 30 seconds to reload!!