14 Rainy Day Outfit Ideas That Are Actually Cute

Look effortlessly cute — even during a downpour.

Person with long black hair holding an umbrella and wearing a light blue jacket and blue and white pants
Photo: Edward Berthelot/Getty Images

Checking our weather app before leaving the house is something we, unfortunately, had to learn the hard way. We can’t even count the times we’ve been caught mid-rainstorm dressed in something fuzzy, furry, or — gah! — white, and those memories of soaking wet shoes and socks are still so clear in our minds.

However, just because we’re now smart enough to expect these showers doesn’t mean choosing something to wear has become any easier. There are rules to keep in mind: no super-absorbent canvas sneakers, ditch light-colored clothing, remember to layer, etc. It can be hard to put together the perfect rainy day look, which is why we've turned to street style in hopes of solving our dilemma.

Ahead, we’ve rounded up 14 cute outfits to wear when it rains, along with some tips on why they'll work.

Go With the Classics

Person outside in the rain wearing a hat, jacket, jeans and boots
Edward Berthelot/Getty Images

Your favorite jeans are a cool and casual choice for a rainy day. Style them with your go-to ankle boots and, if you're feeling daring, try a denim shirt instead of a tee.

Find New Ways to Layer

Person wearing a pink hoodie underneath a long sundress with sneakers
Christian Vierig/Getty Images

If the temperature takes a dip, wear a thin, non-bulky hoodie underneath your maxi dress. Then, you can complete the look with a pair of sneakers for something unexpected and fun!

Don't Be Afraid to Mix It Up

Person wearing a hat, black sweatshirt, black shorts and black combat boots
Edward Berthelot/Getty Images

Typically when we think about shorts, we picture them styled with sneakers or sandals. However, combat boots are also a cute alternative, and will protect your feet should you step in any puddles.

Do a Bit of Color Blocking

Person wearing a yellow jacket, orange pants, peach shirt and black combat boots
Christian Vierig/Getty Images

A gloomy day calls for bright and, more importantly, easy pieces. Grab the most vibrant stuff in your closet and experiment with color combos. A neutral pair of shoes will provide some balance.

Wear a Maxi Dress

Person holding an umbrella wearing a long peach dress, long black jacket and black boots
Daniel Zuchnik/Getty Images

A pair of boots and a long jacket will make the staple work for not-too-hot, not-too-cold days.

Break Out Your Sweats

Person getting out of a car wearing a purple and white plaid long jacket, tan sweats and purple zip-up boots
NurPhoto/Getty Images

You can turn the world's coziest pair of pants into something elevated with the help of a structured button-down, a blazer, and zip-up boots.

Think Outside the Box

Person wearing a printed tunic paired with tan pants, boots and a ball cap
Edward Berthelot/Getty Images

If bare legs aren't an option, embrace the return of the early '00s and style a dress or long tunic over cropped pants.

Remember Your Rain Boots

Person wearing a white button-down shirt, long black jacket, black pants and black and white rain boots
Christian Vierig/Getty Images

Invest in a sleek, short, black pair, which can pass as regular booties if the sun comes out mid-day.

Give Your Outfit a Casual Twist

Person wearing a matching yellow blazer and pants outfit paired with sneakers and an orange bag
Kirstin Sinclair/Getty Images

Not feeling boots? Go with an old pair of sneakers instead. You won't need to worry about them getting messed up, and they'll give your outfit a laid-back vibe.

Add a Hat

Person wearing a plaid hat, long green jacket, jeans and yellow boots
Christian Vierig/Getty Images

Be it a bucket option, a cap, or a beret, it will add flair to your outfit and protect your hair in style.

Reach For Loose Pants

Person wearing baggy khaki pants, a black camisole and jacket paired with colorful sneakers
Jeremy Moeller/Getty Images

You might regret wearing anything formfitting and constricting, especially if you plan to take it easy all day. A baggy pair of khakis will not only ensure you're on-trend, but they'll also look great with a simple tank top and cardigan, too.

Pull On a Blazer

Person wearing a black blazer with a belt, paired with a long black skirt and black boots
Christian Vierig/Getty Images

It's a quick trick that will take any outfit to the next level, adding warmth while ensuring you look sharp. Feel like your outfit is missing a little something? Cinch your waist with the help of a belt.

Try Matchy-Matchy

Person wearing matching tan and yellow button-down shirt with pants and orange shoes
Melodie Jeng/Getty Images

If you tend to feel unmotivated and lazy on rainy days, it's worth adding a matching set to your closet. Now, your outfit is already put together for you (minus shoes), and you'll have less stress while getting ready in the morning.

Keep It Simple

Person wearing a black babydoll dress paired with black rain boots
Christian Vierig/Getty Images

When in doubt, reach for a short black dress and trusty black boots. It's an easy choice that you can then amp up with accessories such as tights, a scarf, and layered necklaces.

Related Articles