Accessories

I don't like travelling when it's right on the cusp of changing seasons. It's really difficult to determine clothing and items to bring. Do I bring the shaving accessories? Hard to tell if it's kind of warm but not really. Do I bring the bathing suit? But it seems so windy. Do I bring the jeans, but it seems like it will get sunny and hot. How about the umbrella? I mean, it could suddenly rain. I know...first world problems and these are good ones to have. Except, it doesn't make packing any easier.