When riding in the rain with your umbrella, you probably don't want to wear a dress or skirt that is going to catch the wind unless you can ride with no hands or you have on very modest undergarments. Unfortunately, I haven't ridden without hands in ages and I don't recall being very good at it. Also, I was wearing very immodest, bright blue underwear that could be seen from a country mile. I had to pull over to the side of the road and stow my umbrella in my basket for the sake of my dignity. I didn't get very wet though; I was almost home.