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.

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. 

This color… I mean, come on.

I’ll need a pair of oversize sunglasses to hide my disgust with the weather.

I just tried these on, and it’s safe to say that I’m obsessed.

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.

I can’t believe I found a quality faux-leather trench that’s under $200.

Seeing this vest styled up with a nice tie, I’m sold.

Love at first sight.

I have these in multiple colors, and I’d buy more.

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.

I need you in my life.

A bodysuit will keep me warm despite the rain.

These are everything.

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.

This vest looks great layered with a tee or on its own. 

I love when my prints almost match but not quite.

Leather weather.

These are so good they made me toss another outdated pair of black boots so I could give them extra room.

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.


This cardigan is absolutely everything.

Off-white jeans are my jam.

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.

This one is so on-trend.

I will buy as many oversize tees as I can.

We love a cargo moment.

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.

It zips in the back for easier layering.

Invest in the basics.

I’m here for the A&F hype.

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