Gene Kelly’s “Singin’ in the Rain” comes to mind every once in a while, when the city’s downpour feels romantic, maybe even a little cinematic. The reality, of course, is far less glamorous: dark skies, rogue splash zones, and the age-old question of what to wear in this weather.

Dressing for a rainy day is one of the trickiest wardrobe feats to master. You want to feel polished, but practical; shielded from the elements, but not too bundled. It’s a delicate balance that feels especially difficult to tread in New York City, when commuting home during a surprise deluge can turn into a full-on obstacle course.

The secret is to start dressing for the rain instead of against it, building your outfit around pieces designed to withstand an erratic shower: a water-repellant trench coat, a durable twill bucket hat, puddle-proof rubber footwear, and a bright accessory that cuts through the gloom.

Below you’ll find some outfit inspiration for the next rainy day forecast—proof that even the greyest of days deserve a good outfit. (P.S. Don’t forget your umbrella!)

Hat Tip

TWP and Gigi Burris teamed on what may be the chicest solution for humid hair: a water-repellant, wide-brim hat in a durable cotton gabardine (the same fabric used for trench coats). Let it lead your look with a tank dress and tall rubber boots. Simple, yet streamlined!

All Clear

Loewe’s PVC bootie, fresh from the spring runway, makes a compelling case for wearing heels in the rain. We’d style them with an anorak, a white tee, and (as long as the temperature allows) Bermuda shorts.

Green Thumb

Go from garden work to walk in park with a car coat, cuffed denim, and Celine’s olive green rubber clogs. Add a sporty cap to shield your hair from the elements.

Splashes of Color

The antidote to a somber day? Vivid color! Take cues from this season’s highlighter brights and go for sensible separates in primary shades—a sporty yellow Prada jacket and cobalt blue turtleneck are a solid match for black tapered trousers. Finish with Alaïa’s leather ballet flats, complete with removable rubber soles.

Just a Hint of Red

Always trust the power of red to brighten up a gloomy day. Toteme’s red trench jacket pairs nicely with everyday essentials like a simple tank, grey sweater, and tailored slacks. Ground the look with a lug sole loafer for a polished finish.

Technical Expertise

Go sporty for a packed Saturday with non-stop spitting rain on the forecast. Build your look from the ground up with a gorpcore sneaker, adding on a berry-hued blouson and technical skirt. It’s an unfussy look to help you check off all the to-dos on your list.

The Perennial Favorite

The waxed jacket of choice for Upper East siders and English countryside-goers hoping to brave inclement weather without losing their sense of style. Pair with straight-leg denim, a bright button-down, and Loeffler Randall’s lug-sole Chelsea boots for a sleek yet effective ensemble.

Playful Minimalism

Louise Trotter brings the water-resistant garden clog into high fashion territory with a sharp PVC style in Bottega green. We love the idea of contrasting it with minimalist separates: a sleek midi skirt, ruched top, and Toteme’s technical jacket layered on top. Permission to leave your umbrella at home with this one—the jacket’s scarf attachment is also a convertible hood.

Office-Ready

For a more polished approach to rainy day office wear, swap floor grazing rousers for capris to avoid soaked hems. Add a blazer and Burberry’s Castleford maxi trench, completing with ballet flats or a sturdy low pump plus a trusty umbrella, natch.