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

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

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

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

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

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

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

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

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

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

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

You might regret waring 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 for 2020, they'll look great with a simple tank top and cardigan, too.

Pull On a Blazer

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

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

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 accessorires such as tights, a scarf, and layered necklaces.

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