Bicycling with an umbrella is quite popular in Holland, despite the wind. Here are a few girls demonstrating the classic style. There are now sleek umbrellas specially designed for the purpose that are a bit more aerodynamic. The pink colored clothes in the images are for the gay pride parade which had just finished before these were shot.
Notice how her umbrella is buckling under pressure. The heels and bag over the shoulder are nice touches.
Fairly classic. Note the cyclist with umbrella going down the other street behind her.
She looks like she’s struggling a bit. Using a U-lock, which is pretty uncommon here.
Of course, when I tried it, my Indian umbrella was immediately turned inside out and one of the metal points popped out. I also found it a bit tricky to ride with only one hand. Keeping the hand next to the bell free is probably more important than the shifter. Since my bicycle has handlebar brakes, this also compromised my ability to brake quickly so starting and stopping were more complicated.
Apparently, this is also quite common practice in Japan. Haven’t seen it much in Denmark.