I Live in NYC, so I Know How to Dress for the Rain—6 Outfit Formulas I Recommend

Sierra Mayhew's avatar
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in How Tos
Kelsey Merritt carrying an umbrella.
(Image credit: @kelseymerritt)

When it rains, it pours.

I'm guilty of letting bad weather get to me, and a rainy day can often lead to ensembles comprised of sweatpants and oversize tees that make it easy to get out the door. That cycle ends today because I've just pulled together the ultimate mood board for dreary weather that will immediately brighten anyone's day.

One of the keys to success when it comes to rainy-day fashion is to always be prepared. When you have items set aside just for a rainy day, it can feel exciting to pull them out. Weather-friendly lug-sole boots that have a coordinating bag are always a good idea, and my favorite umbrella that I collected at a fashion internship many years ago is always my special guest. The outfits I've selected are going to help me add many new items to my repertoire that I can wear in a multitude of ways. These six looks deserve a spot on your Pinterest board.

Woman wearing a rainy-day outfit.

(Image credit: @chrissyford)

All you really need to survive a rainy day in style is a very good trench coat and knee-high boots. I reserve the best of the best for these occasions, so picture something that has a unique color, belt, or collar.

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Woman wearing a rainy-day outfit.

(Image credit: @kelseymerritt)

Layers on layers are another survival technique for the rain. Rainy weather sometimes means higher temperatures than we usually see in the fall and winter, so layering up will help you stay dry but also look chic underneath it all.

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Amy Lefevre wearing a pink sweater, tan trousers, and tall black boots.

(Image credit: @lefevrediary)

If you're having a bit of trouble pulling yourself into something that feels stylish when the rain is coming down, try leaning into an easy trend to wear, like a pop of pink. A splash of color on a gray day will never fail to put that smile back on your face.

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Woman wearing a rainy-day outfit.

(Image credit: @_sierramayhew)

I'm telling you layers are the answer. When it's not raining too, too much, an opportunity to wear a leather jacket arises. The lug-sole boots are the perfect finishing touch.

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Woman wearing a rainy-day outfit.

(Image credit: @claire_most)

It's time for your puffer vest to shine when the weather takes a dreary turn. I love pairing it with similar colors to create a very interesting look.

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Woman wearing a rainy-day outfit.

(Image credit: @emilisindlev)

Oversize bomber jackets are having a very big moment right now, and I'd like to bring mine with me everywhere. They easily repel rain and are the perfect outerwear staple for the difficult-to-dress-for weather.

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Sierra Mayhew
Sierra Mayhew
Fashion Editor

Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of industry experience to the editorial team. Since joining in 2021, she has made her mark by blending luxury and accessible fashion, decoding runway trends, and curating must-have shopping lists. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. A graduate of the University of Notre Dame, Sierra translates editorial expertise into viral social content, making fashion engaging for a new generation. Her unique perspective is rooted in her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.