7 Things I Always Wear When the Weather Sucks


(Image credit: Edward Berthelot/Getty Images)

Bad weather—especially in the fall and winter—is inevitable. Call me crazy, but I actually like icky days and look forward to busting out my all-weather gear for the occasion. I don't have a huge collection of gross-weather clothes, as I don't exactly live in Seattle, but I like to keep stylish versions of the essentials on hand for when it's particularly damp outside. And many of these essentials can certainly be worn when the weather doesn't suck, so don't worry about their use being limited.

Below, you'll find a list of my go-to gear for when it's cold and wet outside and the most stylish versions within each category. From jackets to accessories to the coolest all-weather shoes on the market, these will have you covered (literally) for the rainy season ahead. Many of these items will also work for blustery winter weather. As they say, stay dry out there!

All-Weather Shoes and Boots

Stylish waterproof boots and clogs aren't hard to come by these days, and plenty of them are subtle enough to be worn inside. 

Shop All-Weather Shoes

The North Face Jackets

When it's cold and wet out, all I want to do is put on a cozy North Face puffer. They're super lightweight yet warm, as they're filled with down.

Shop The North Face Jackets

Non-Puddle Pants

This season has been all about puddle pants, also known as pants (or jeans) that are long enough to pool around your ankles and drag on the floor. Obviously, this isn't ideal when the ground is wet. Instead, I go for slightly cropped styles that'll stay dry.

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Hoodies are great on rainy days, as they keep your head dry in the absence of a hat, plain and simple.

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Compact Umbrellas

If the umbrella isn't tiny yet mighty, I don't want it. I prefer ones that I can easily throw in my bag, suitcase, or jacket pocket.

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Nylon Bags

Nylon bags, in all their '90s-era glory, are great for crummy weather. I don't know about you, but I don't want water spots on my leather bags.

Shop Nylon Bags


No one wants to contend with rain-soaked hair during their daily commute. Grab a cute hat on your way out the door, and at least part of your hair will remain dry.

Shop Hats

Next up, 36 Epic Sweaters I Want From J.Crew, H&M, Zara, and Mango

Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.