I Live in NYC, so I Know How to Dress for the Rain—7 Outfit Formulas I Recommend

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.

Over the years, I've collected items that I gravitate toward when it rains. Lug-sole boots that have a coordinating bag are immediately slipped on, and my favorite umbrella that I collected at a fashion internship many years ago is always my special guest. The outfits I've selected below are going to help me add many new items to my repertoire that I can wear in a multitude of ways. These seven looks deserve a spot on your Pinterest board.

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(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 types of occasions, so picture something that has a unique color, belt, or collar. 

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(Image credit: @ariannabaq)

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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(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 monochrome. Matching your jacket to your pants will always make for a polished 'fit.

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(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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(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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(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 so make for the perfect outerwear staple for the difficult-to-dress-for weather.

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(Image credit: @mariaalia)

You know a woman is sophisticated when she's able to pair a Y2K tube top with a classic button-down shirt. This is a look I'd love to try next.

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Sierra Mayhew
Fashion Editor

Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of experience in the fashion industry to the editorial team. Since joining Who What Wear in 2021, Sierra has made her mark by expertly blending luxury and accessible fashion content. Whether she's decoding the latest runway presentations or crafting a perfectly curated shopping list, Sierra's keen eye and relatable approach have solidified her as a trusted voice in the fashion space. She's also reported on major industry events like Paris Fashion Week and lent her expertise to red carpet coverage, ensuring her audience gets an insider's view of the most glamorous moments in style. 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. Her ability to translate editorial expertise into viral social media content sets her apart, seamlessly bringing her articles and personality to life for a new generation of readers and followers. A graduate of the University of Notre Dame, Sierra brings a unique perspective to the fashion industry that is informed by her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.