When the city’s downpours feel romantic, even a little cinematic, Gene Kelly’s “Singin’ in the Rain” comes to mind from time to time. Of course, the reality was far less glamorous: dark skies, rogue splash zones, and the age-old question of what to wear in this weather.
Dressing for rainy days is one of the hardest wardrobe tips to master. You want to feel elegant yet practical; protected from the elements but not too restrictive. It’s a delicate balance that can feel especially difficult in New York City, where getting home during sudden flooding can turn into a full-blown obstacle course.
FashionFavorite rainy day essentials
The secret is to start with dressing for Avoid the rain, rather than fight it, and build your outfit around pieces that can withstand erratic showers: a waterproof windbreaker, a durable twill bucket hat, pit-proof rubber shoes, and bright accessories that cut through the gloom.
Below you’ll find some outfit inspiration for the rainy weather forecast, proving that even the grayest of days deserves a good outfit. (PS don’t forget to bring an umbrella!)
hat tip
TWP and Gigi Burris teamed up to create the chicest solution to damp hair: a waterproof wide-brimmed hat made from durable cotton gabardine (the same fabric used in trench coats). Let it lead your look with a tank top and tall rubber boots. Simple, yet streamlined!



