Rainy Day Outfits Ideas- 30 Cute Ways to Dress on Rainy Days

Rainy Day Outfits Ideas. Cold and wet fall days are now upon us and winter is soon to follow. For many, those long, drizzly days can be a serious downer. For others, they are a major inconvenience. After all, what does one wear on a rainy day other than their grubbiest clothing – stuff they don’t mind getting wet or muddy?

If all those upcoming gray days are bumming you out, don’t you worry. Here at Outfit Trends, we have compiled 30 cute and stylish outfits that will have you feeling cheerful and looking your best! Bookmark this page and next time a rainy day is getting you down, have a little scroll through and pick out an outfit you can pull from your own closet and throw together. The rainy days don’t have to win, ladies!

What to Wear on a Rainy Days

Here are some quick tips to keep in mind when dressing for rainy weather or dealing with unpredictable weather in general.

  • Say adios to boring old galoshes and invest in some cute rain boots so that no matter what outfit you are wearing, you can feel stylish and put-together. There are so many options these days when it comes to rain boots so consider getting yourself a nice pair that you’ll always feel great in. (Pro tip: knee high boots will keep you dry and look great with skinny jeans!)
  • Consider adding a scarf to your look to protect your hair. Rainy days can be tricky but rainy and humid days are trickier. A thin scarf to tie around your hair can keep flyaways at bay and protect against frizz.
  • Layer your outfit in case of a sudden change of weather. Nothing is more frustrating than dressing for light rain and encountering sleet, or wrapping up warmly for a freezing day only to see the sun suddenly come out. If rain is on the radar then layer your outfit so that you can ditch outer layers if it suddenly gets warm and dry or to keep yourself warm in case the weather takes a turn for the worst.
  • Always keep an umbrella stashed in your purse or car. You won’t regret it!

Here are 30 cute ways to dress on a rainy day.

what to wear on rainy day

↓ 30 – Sock Boots and Leather Jacket

Right out the gate, we want to show you a super cute outfit you can feel totally yourself in, no matter what the sky is throwing at you. From the comfy hoodie to the edgy jacket and Givenchy rubber sock boots, this outfit is so 2020… in a good way! Whether or not Givenchy boots fit your budget, this look is easily replicated and a breeze to throw together. Just add an umbrella and you are good to go!

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↓ 29 – Colorful Scarf and Bright Pink Rain Boots

Do rainy days have you feeling glum and gloomy? Us, too. So why not pull out all the stops and give yourself an instant mood boost by wearing the brightest, most cheerful colors you can find? There is a real psychology behind what we wear having an effect on our mood. And it’s hard to feel bummed out when wearing bright pink rain boots like these! Plus, you can accessorize with gorgeous earrings and colorful scarves too, so feel free to go all out and let your inner toddler have a field day. And while you’re at it, how about hunting down a good rain puddle or two and having a nice old-fashioned splash? You’ll be feeling better in no time.

Colorful Scarf and Bright Pink Rain Boots


↓ 28 – Cute Party Look

Headed to a party but it’s wet, drizzly kind of day or evening? Not to worry. This cute look will cover you up without sacrificing your party vibes. Simply tuck a tee (we love this “First Of All, No” shirt) into a short leather skirt and pop a raincoat or light jacket on top. For footwear, knee-high boots will keep your feet dry and your legs warm. Worried you’ll still be cold or wet? Add some tights to the ensemble!

Cute Party Look


↓ 27 – Classy Trenchcoat and Chunky Boots

There is something so classy and chic about a warm brown trenchcoat over a black outfit. From the eye-pleasing neutrals to the Parisian style of stripped-down glamour, this stylish ensemble gets all the heart eyes. Perfect for a cold, drizzly fall day, this easy-peasy look will have people thinking you are a bonafide fashionista! Simply layer a black crewneck sweater with a long, brown trench and pair it with some faux leather leggings. Throw on some rainboots or chunky lace-up boots, if the weather allows for it. Accessorize with a black leather purse and a simple silver necklace.

Classy Trenchcoat and Chunky Boots


↓ 26 – Runway Ready

Feeling like you want to pull out all the stops? Here’s how you can look runway ready. Wear a short dress with synthetic tights and a burgundy leather coat. Finish the look off with black ankle boots and a shoulder bag. A swipe of red lipstick and you are in business.

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↓ 25 – Long Coat

Wear a long coat with a black shirt and trousers and black long boots with a black bag. Here are some more Long Coat Styles that you should try.

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↓ 24 – Sunshine Yellow

Wear a striped shirt with jeans and long leather boots. Add color by wearing a yellow leather trench coat and you are good to go!

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↓ 23 – Gorgeous Florals

Pair a neutral colored shirt with black tights and long boots with a super cute frock style floral jacket. We promise it will cheer you up, even on the grayest winter day.

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↓ 22 – Patterns and Denim

Here is a fantastic option for a rainy humid summer day… a patterned dress sans tights will keep you feeling fresh and cool. Swap out a drab black umbrella (though that can be chic in its own way) for a see-through one which will pair well with anything. (Making your umbrella a part of your outfit is a good way to level up your style.) If there is a nip to the air, add a denim jacket. Lastly, chunky ankle boots will keep your feet dry and will keep you feeling cute and stylish.

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↓ 21 – Scalloped Skirt Suit

Feeling brave? Go all-white and try a scalloped skirt set and Mary Janes with a shoulder bag. A bright blue umbrella will cheer up your whole ensemble as well.

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↓ 20 – Casual and Simple with Cropped Pants

A denim jacket layered over a striped knit and faded army green pants with ballet flats. Casual yet cute.

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↓ 19 – Photoshoot like a Gossip Girl

An oldie but a total goodie! Dress like your favorite Gossip Girl character by wearing a patterned skirt with a sleeveless crop top and high heels (only for photoshoots though… heels aren’t usually a good option for rainy days!). Here are some more of my favorite Gossip Girl Outfits.

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↓ 18 – Humid, Rainy Day Outfit

Another throwback look we still love. A loose, flowy dress (just long enough to prevent any unfortunate flashes) will keep your feel light and cool. These “ugly-pretty” buckled slide-ons are comfy and practical.. and work best after a rainfall, not during. Plus, if you add a cute umbrella, you’ll be tying the look together in a totally fashionista-approved way.

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↓ 17 – Casual-Chic Street Style

Look chic in a faded shirt and jeans with nude sandals (if it’s just a drizzly day) and a bag.

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↓ 16 – Black and White with Long Boots

Wear a white dress with black boots, a black bag for a perfect rainy day look.

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↓ 15 – Styling Red on a Rainy Day

Pair a black shirt with black leather pants and a skin leather jacket with bold red sneakers and a handbag.

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↓ 14 – Rainy Day in Striped Shirt

Wear a black and white striped dress with a white trench coat, red bag, and your choice of cute rain boots.

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↓ 13 – Layering Up on Rainy Days

Layer your look with a striped shirt topped with a knitted sweater shirt topped with a windbreaker jacket with simple jeans and a handbag.

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↓ 12 – Celebrity Style All Black Outfit

Wear a black shirt with a black leather coat and pair it up with a black short skirt and leggings as well as black leather ankle boots. Finish up with a black handbag.

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Love wearing all-black outfits? Then don’t miss out on these 25 Celebrities All Black outfits Styles for Fall to Copy.

↓ 11 – Fashionably Baggy

Wear a cream crop top with cream trousers and finish the look off with a super long trench coat and brown boots. This fashionably baggy look is in a class of its own.

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↓ 10 – Oversized Green Jacket

Wear a turtleneck with a black jegging and a zip-up hoodie with black ankle boots. Here are some more fabulous Ideas on How to Wear Hoodies.

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↓ 9 – Street Style Patterns

Pair these leopard print pants up with a blue shirt, cherry color shoes (we don’t recommend heels), and an envelope handbag. Different patterns and yet it totally works.

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↓ 8 – Oversized Outfit for a Casual Look

Wear an oversized white sweater on an oversized tunic with over-the-knee boots. Here are some more fabulous ideas on How To Wear Oversized Clothes.

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↓ 7 – Classy Coat for Rainy Winter Days

Look classy by wearing this elegant cream and black coat, light blue jeans, and brown rain boots.

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↓ 6 – Coffee Date Look

If you have a coffee date planned with your gal pals, this cute look can be a lifesaver. Just throw on a polka dot button-down over jeans and some bright pink wellies. A beige purse and blue umbrella tie the look together.

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↓ 5 – Work Attire

On a working day wear a gray shirt with a blue blazer and blue and polka-dotted pants. You may do better with some cute ankle rain boots over flats though! For more ideas, here’s our complete collection of Outfit Ideas on What to Wear to Work On Rainy Days.

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↓ 4 – Baggy Bright Yellow Coat

Wear it in yellow and pair it up with a black shirt, bag, and high heel long boots. And don’t forget a funky umbrella like this cheetah-print bad boy!

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↓ 3 – Last-Minute College Girl Look

Say you woke up late and you are in a hurry. You glance at the weather app on your phone and see that there’s going to be scattered showers throughout the day… what do you do? How about sticking a pin in the old jeans-and-tee look and going for something totally cute and easy to throw on? All you need is a pastel-colored tee to wear under a navy blue jumper dress. Add tights and some cute rain boots. And there you are! A girly but totally easy look you can create in one, two, three… done!

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↓ 2 – Bright Prints for April Showers

Go bold by wearing a bright printed outfit and printed shoes in spring.

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↓ 1 – Opt For Sneakers for a Rainy Day in Fall

Bored with tall boots? Opt for sneakers with a skirt outfit.

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Frequently Asked Questions

Here are some frequently asked questions about what to wear on a rainy day, how to look cute, plus what not to wear when it’s raining. Check them out!

Q. What should you not wear on a rainy day?

A. There are a few hard-and-fast “rules” for rainy days. When in doubt, you can fall back on these rules to avoid any unfortunate wardrobe mishaps! Here are the top five things you shouldn’t wear on a rainy day:

  1. Heels. This is a pretty obvious one but heels are just not a great idea on rainy days. Not only will you ruin your probably pricey footwear but your feet will get soaking wet. No thank you.
  2. Suede or velvet. Both will get ruined if wet.
  3. White… most of the time. You might have noticed we included an all-white outfit in this article. That’s because once in a while, we like to encourage our readers to live on the edge! 😉
    However, white outfits aren’t usually a good idea for two reasons:
    a) they are more prone to stain
    b) they can become see-through when wet.
  4. Open purses or bags. Not only are they a pain to keep out of direct rainfall but a little bit of rain can do irreparable damage to many of your most cherished items! Always carry a closable purse when dealing with wet weather.
  5. Regular mascara. Waterproof always, baby!

Q. Are jeans okay for rainy days?

A. Yep! For light rain, jeans are fine. For heavier rain, look for slim-fitting, lightweight, quick-dry pants. Opt for a dark color so as not to show stains or dirt.

Q. How can I look cute in the rain?

A. We sure hope this article gave you some ideas! But here are three tips for looking cute in the rain:

  1. Wear red lipstick. It’ll make you feel like a million bucks.
  2. Wear cute rain boots. (And a nice trenchcoat if it’s cold.)
  3. Use hairspray to keep flyaways from taking over your hairdo and always wear waterproof mascara

And that’s it! We hope this article gave you plenty of ideas for what to wear on rainy days… and how to look cute at the same time!

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