Gustave Caillebotte painted Paris Street; Rainy Day in 1877, and it still hangs at the Art Institute of Chicago: wet paving stones, gray light and a whole street dressed well under umbrellas. Inspired by that canvas, by the sound of rain on a window and by a black umbrella dripping in a doorway, this is what I wear when it pours. It starts with the trench, and a long one from Toteme, Phoebe Philo, Saint Laurent or Burberry covers more of you than any jacket.

Under the trench, go dark. A black sweater and dark jeans hide rain spots and splashes, and they look sharp against a khaki or olive coat. Eterne's Francis cashmere crew and Anine Bing's Imane sweater are the easy picks, and Loulou de Saison's Kaia cardigan layers well if the day turns cold. For jeans, a straight dark wash like DÔEN's Ondine or Tibi's selvage Alec jean works with boots. Roll the hem once if the street is wet.

Shoes decide whether a rainy day is fine or miserable, so wear a boot. Khaite's Colt ankle boot and Zimmermann's knee-high Alchemy boots both sit under a trench without fuss, and Christian Louboutin's patent Miss Z shrugs off water. Carry a tote deep enough to keep things dry, like Anine Bing's Elly or Balmain's Sphynx. What I would skip: pale suede shoes, a hem that drags on the ground and any bag you would be sad to see soaked.