Thank you for showing this inspirational outfit! You look VERY chic and sophisticated.
I agree that it can indeed be a challenge to look stylish in rain gear.
As for myself, I have always found solid black umbrellas extremely boring and sad-looking, so I have acquired a collection of bright and patterned umbrellas to cheer me up on rainy days. (Even at funerals, you will not see me under a solid black umbrella. I will prefer a tasteful black-and-white or navy-and-white pattern.)
I am the happy owner of an azure blue self-patterned rain coat with tiny ruffles along the high-low hem. A treasured gift from a dear friend. The colour and the fun details always make me and others smile.
Except for garden work, hiking, etc., I want to avoid frumpy-looking wellies. As I often wear dresses and skirts, I have been on the outlook for a pair of CHIC LONG rain boots. I am very pleased with my recent purchase: deep blue long rain boots with shafts in a quilted look (á la Chanel's quilted bags). They will look great year round in most (wet ) surroundings.