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.

rainy-day-outfits-303268-1666800006437-main

(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. 

Shop the look:

rainy-day-outfits-303268-1666799760465-main

(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.

Shop the look:

rainy-day-outfits-303268-1666800557000-main

(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.

Shop the look:

rainy-day-outfits-303268-1666798764889-main

(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.

Shop the look:

rainy-day-outfits-303268-1666800787479-main

(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.

Shop the look:

rainy-day-outfits-303268-1666802167975-main

(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.

Shop the look:

rainy-day-outfits-303268-1666802694998-main

(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.

Shop the look:

Up Next: It's True—New York Women in 2022 All Own These 6 Things

Associate Editor

Sierra Mayhew was always destined to work in fashion, but she didn't know it at first. Growing up with no choice but to wear a rotation of school uniforms and activewear, her love for fashion really blossomed when she moved away for college and was able to finally define her very own personal style. Shortly thereafter, she interned at Elle magazine and instantly knew that editorial was for her. After graduating from the University of Notre Dame, she worked for ShopBazaar, contributing regularly to Bazaar.com, and finally made her way to Who What Wear, where she is an associate editor. When she’s not working, you can catch her always trying to catch a flight, trying the latest fitness craze in New York City, or exploring luxury vintage boutiques.