What to Wear on a Rainy Fall Day

What to Wear on a Rainy Fall Day

What to wear on a rainy fall day: a trench, a dark knit, dark jeans and boots that can take a puddle. I pair trenches from DÔEN, Toteme and Gucci with dark knits, then finish with boots and a tote.

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.

Flat lay of a brown trench coat, a black sweater, a black cardigan, blue jeans, black knee-high boots, brown and black ankle boots, a black leather tote and a burgundy leather tote on white.
The rainy day kit: a trench, dark knits, jeans, boots and a deep tote.

Trench coats

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.

Dark knits and jeans

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.

Boots and totes