The 4 Rules of Dressing for a Rainy Day, According to Women Who Live in Some of the Rainiest Places in the U.S.

“I find that denim and cotton tend to get wet and stay wet, so I avoid them if I can,” says Delmonte. Indeed, cotton is incredibly absorbent but not very quick to dry, so if you accidentally get soaked, you’re likely to stay that way, especially if you opt for thicker, rigid jeans over a thinner linen pant. McCulloch also suggests avoiding fabrics that might be damaged by errant rain drops like faux fur, suede or puffers that haven’t been treated for weather-proofing. “I opt for densely woven synthetic materials, a classic trench coat in a fun color or something like a coated faux leather jacket that will repel the moisture!” As for Agraviador, she’s a big fan of wool, which will still keep you warm even when wet, and stresses the importance of investing in water-repellant outerwear.

Our two cents: Look for clothing made from sporty, tech-focused materials that wick away moisture and dry quickly. There are lots of brands, like Athleta and Aday, that make professional, chic-looking clothes that are secretly great at wicking away sweat or, in this case, rain water to keep you comfy all day long.

This, of course, comes down a bit to personal taste, but all three of our experts agree rainy days are not the time for maxi dresses, wide-leg pants or flared jeans. If you’re a pants gal, try a straight-leg or skinny fit that hits right around your ankle to prevent soaking wet hems. For skirts or dresses, McCulloch suggests midi lengths, which similarly won’t soak through from the ground up but also won’t cause a Marilyn Monroe moment when the wind suddenly gusts through. As for coats, Delmonte says long is the way to go. “The more of you that’s covered by a trench coat or slicker, the better. Even if you pick a jacket that hits just below the hips that means your bum will stay dry in addition to your arms and torso, which is great.”

Which is better, raincoats or umbrellas? Short answer is whatever is most convenient for you. Despite Chicago’s gusty reputation, McCulloch is team umbrella for the sartorial opportunities. “It can be another accessory for your outfit! I have a collection of bright, colorful umbrellas and it makes me so happy on rainy days to choose which one to pair with my outfit.” Agraviador, on the other hand prefers the minimalism of a raincoat. “I have never really carried an umbrella because I don't like to carry a lot of things…I’m team raincoat all the way.” For the tie-breaking vote, Delmonte is also team raincoat, albeit with one small note. “I like having my hands free and not having to worry about potentially leaving my umbrella behind someplace, but with raincoats it’s super important to find one with a great hood. It needs to come out far enough over your face to act like a hat brim and should have a cord so you can pull it in tight in case of wind. I’ve tested a whole bunch of raincoats over the years and usually end up adding a baseball cap underneath to better protect my face.”

Shop raincoats: ASOS Curve Rain Parka ($55); Columbia Sportswear Lillian Ridge Shell Jacket ($120); The North Face City Breeze Rain Parka ($179); Stutterheim Mosebacke Coat ($325); Patagonia Granite Crest Jacket ($279); Ulla Popken Triple Function Rain Jacket ($150)

Shop umbrellas: Weatherman Travel Umbrella ($69); Certain Standard Umbrella ($75); Balios Travel Umbrella ($27); Kate Spade New York Rain Check Umbrella ($38); Old Navy Compact Umbrella ($12); Repell Windproof Travel Umbrella ($30)

The two best options are to invest in whether-proof boots that don’t look like your usual Wellies, or to steer into the skid and allow your bright, bold boots to really steal the show. “I'll pick a bright, fun pair of rain boots, add knee socks in a pattern or contrasting color and wear a layered outfit with a knee-length skirt,” says McCulloch, although most of the time she prefers the ease of a block-heel leather bootie that has been treated for weather protection. “I’ve you’re willing to splurge, La Canadienne is like the Holy Grail of stylish, weather-ready footwear,” says Delmonte, “but Blondo also makes some super cute rain boots that are much more affordable.” And Agraviador swears by her Everlane Chelsea booties that go with basically everything in her wardrobe.

Shop rain boots: Blondo Nanite Ankle Boots ($160); La Canadienne Paton Leather Boots ($595); Sorel Brex Waterproof Chelsea Boots ($160); Schutz Lace-Up Rain Boots ($138); Dolce Vita Huey H2O Boots ($140); AquaDiva Florence Over-the-Knee Boots ($235)