30 Best Rainy Day Outfits for Men and Women [2024 Guide] (2024)

When summer hits, you’re probably looking up all kinds of outfit ideas for festivals, and warm, summer days. You’re imagining pulling out that cute summer dress from the back of your closet, throwing on white sneakers, and creating a super cute look with your favorite bikini on the beach.

What you certainly aren’t imagining is jackets, rain boots, leggings and anything else that just screams winter. But, the flowers and grass need rain, so inevitably we must deal with a few rainy day outfits during the summer season.

But, don’t be discouraged! Rainy day outfits can also be super stylish! Admit it, you’ve been dying to throw on your favorite trench coat.

Men’sRainy Day Outfits

1. Casual Rainy Day Outfits

If you’re the type who doesn’t like to get your best shoes all wet or get mud on the bottom of your dress pants, you’re probably thinking you have to trade in your fashionable status for a frumpy, cold weather look. But, fret not! You can dress casual and still look super stylish and put together.

A casual rainy day outfit is all about drawing eyes to your jacket and keeping the rest of the outfit simple. A white turtleneck with dark jeans and ankle boots is a great start, but you can really wow people with a wool jacket in a bright color like red. Another great way to stay warm and stylish at the same time is layering. Stick with pieces in a similar color tone that compliment one another.

Dark green pants with a simple t-shirt and button down look super trendy under a stylish wool jacket. Your outfit doesn’t have to be boring to be casual either; simply add some noticeable accessories. White ankle boots are way different than the normal black and brown people are used to seeing, and a hat adds a bit of sophistication to an otherwise super casual look.

2. Hipster Rainy Day Outfits

You may be thinking of a hipster outfit as being more for summer, with festival season showing off the best of them, but a rainy day can include this style as well. Lots of layers, interesting shoe choices, and thrifted jackets make for a unique look, even when the rain might have you questioning your fashion choices.

For the more mysterious hipster rainy day outfit, a black leather jacket adds some texture to more simple pieces like a plain black t-shirt. Keep it sophisticated with a pair of soft, gray dress pants.

If you like black but want to add a little more flare to your rainy day outfit, try a shirt in an interesting pattern, even better if the shirt doubles as a jacket so you don’t have to add so many layers. If you have a loose, oversize shirt on top, stick with tighter skinny jeans on bottom.

While many rainy day outfits are darker, you can break up all that black with a patterned jacket and perhaps a pair of tan ankle boots to draw the eye to the entire look.

Or you can try opposites, wearing a heavy black Jean jacket over a simple white t-shirt.

3. Smart Casual Rainy Day Outfits

When the weather is rainy, you may be worried about dirtying your favorite fancy shoes, or getting your dress pants wet. But, you can still look fancy while wearing somewhat casual items. A smart casual rainy day outfit is the perfect mix of sophistication and dressing for the weather.

Start with a simple black turtle neck to keep out the cold, and match it with a pair of wool dress pants. A rain jacket doesn’t have to be super sporty, a longer piece in black is a rainy day closet staple and matches with a casual pair of boots or a fancier loafer.

A smart casual rainy day outfit doesn’t have to be dress pants and a sport coat. An elegant, thrifted jacket in a wool material can make a pair of blue denim jeans look super smart. Add a black turtleneck for maximum luxury.

If you’ve got a designer jacket you’re dying to show off, a rainy day is the perfect time. To really draw all eyes to a tan jacket, wear an all black outfit; turtleneck, skinny jeans, and boots.

A smart casual rainy day outfit doesn’t have to mean a super sophisticated jacket either. A black leather jacket with dress pants and loafers can also exemplify the look.

4. Street Style Rainy Day Outfits

Often we think of rainy day outfits as being plain and simple, with dark colors, boring textures, and jackets that make us look like a marshmallow. However, a street style rainy day outfit is all about being unique even when the weather is dull.

Keep the basics of your outfit super chic and simple with black pants, and a brown turtleneck. But, really go for it with the accessories, adding a black, leather jacket and a pair of sports sneakers that show off cool, patterned socks underneath. Or, try the same look with blue, denim jeans and a fanny pack as your accessory to spotlight.

You can make things a little sport by wearing a black hoodie underneath your long, wool jacket, accessorising with a black beanie; the perfect mix of casual and dressy.

You can also keep the whole look sporty, wearing a gray hoodie underneath a black, leather jacket and sports sneakers. Of course, a rainy day outfit doesn’t have to be completely black. Pair a brown turtleneck with a lighter brown jacket and a pair of blue, denim jeans to keep things light.

5. Vintage Rainy Day Outfits

A rainy day outfit doesn’t have to be one or the other: super casual or luxuriously sophisticated. It can be a mix of vintage, thrift store finds and unique boots or fancy jackets.

A long wool jacket is the perfect starting place, especially because you can play around with a variety of colors like dark green. Pair this with a pair of laced up, black leather boots.

If you have found a wool jacket in an eye catching pattern, like plaid, pair it with black skinny jeans to keep the rest of the outfit simple. Wear a pair of ankle boots in a similar color.

Try going for pieces that are all from a similar color family. If you’re starting out with a gray jacket, match this with blue denim jeans, a striped sweater that also includes some blue and gray, and accessorise with a hat also in the same tones. Or, maybe you prefer an earthy color palette. Starting with a tan jacket, pair it with a dark red shirt, and brown boots. A pair of gray jeans breaks up all the desert tones.

Of course, going with an all black outfit can really draw all eyes to your jacket if that’s what you’re hoping for.

Women’s Rainy Day Outfits

1. Casual Rainy Day Outfits

When the skies turn dark and the sun is hidden away, it can make you feel like you want to hide away too. If you would rather curl up on the couch and watch Netflix in your sweatpants on cold, rainy days, nobody would blame you. But, a rainy day outfit can be casual and comfortable, yet still fashionable at the same time.

An oversize, faux fur jacket feels like wrapping a warm, fleece blanket around your shoulders, yet makes you feel like Beyonce; now that is a win! Pair this with simple, black leggings and tall, black boots.

For maximum comfort, a pair of knee-high boots looks chic yet doesn’t appear as if you’re trying too hard. Wear them in a lighter color and go for a darker outfit to draw all eyes to them.

If you really want to dress for the rain specifically, why not show off a pair of Hunter galoshes? Keep the rest of your outfit simple, like an oversize sweater and leggings for extra comfort. You can go straight from the cold, rainy outdoors to chilling in the couch. You can also wear a pair of leather pants if you want to keep the comfort but still look sophisticated.

2. Hipster Rainy Day Outfits

A rainy day doesn’t have to mean trading in your personal style for drab, dull clothing. Rather than fighting against the weather, why not work with it?

Try an all black outfit, like a casual skirt, tights, and cotton t-shirt with simple black ankle boots. To give your look some edge, accessorise with a matching oversize, button down shirt or jacket and a hipster hat.

For a more casual hipster outfit, it’s all about the layers. A sporty jacket with fur trim, over a hoodie and jeans can be a little too simple, but accessorised with a bright beanie, laced up boots, glasses and a designer bag can truly make it a rainy outfit.

Bad weather doesn’t mean you can’t wear a super feminine or chic outfit. But, a pair of knee-high black boots paired with a tight black shirt and skirt is sophisticated. And, a fashionable black hat really pulls together the whole look.

Of course, an outfit can be a mix of hipster feminine and casual at the same time. A simple pair of black skinny jeans paired with a stylish pair of ankle boots is chic, but you can make it casual with a denim jacket.

3. Smart Casual Rainy Day Outfits

So, you’re a super sophisticated fashionista and the rainy weather has you thinking you need to trade in the best items from your extensive closet, but think again! A smart casual rainy weather outfit is all about versatile pieces that look dressed up yet still work in the cold, wet dreary streets.

For starters, choose a pair of black, tall boots that look super dressy and can still be worn when there’s puddles all over the place. And, just because it’s cold out doesn’t mean you can’t still wear a skirt. A long, silk skirt pairs beautifully with a white button down shirt, which is easily the best smart casual uniform.

When it’s cold outside, a jacket cinched in at the waist with a belt can also double as a dress when paired with tights and riding boots. You can still wear a shorter skirt when you pair it with tall boots and a chunky, faux fur jacket on top. You can keep things super feminine if the jacket is a soft pink color, and you accessorise with a girly purse.

4. Street Style Rainy Day Outfits

Street style can still include lots of layers and unique pieces, even if the weather is making it seemingly hard to dress in a stylish manner.
A mix of sporty, casual and fancy is what Street style is all about, and rainy weather shouldn’t change that.

A trench coat is a great place to start; it’s chic, versatile, and goes with everything whether your outfit is super dressed up or dressed down. Pair it with black, leather pants and ankle boots that work on wet ground. Give the outfit a more casual feel with a sporty baseball hat.

Just because it’s raining doesn’t mean you have to trade in your most stylish boots for simple black ones. A pair of white ankle boots dresses up a simple outfit of jeans and a white shirt.

You can also keep your outfit darker if that’s what you prefer on rainy days; a trench coat doesn’t have to be tan, you can also wear a black one. Paired with simple blue jeans and a white turtleneck, you have lots of room for accessorising; a black hat will give you a little bit of mystery.

5. Vintage Rainy Day Outfits

Vintage rainy day outfits can include thrifted pieces, dark colors, lots of patterns, and fun accessories. A black leather dress is the ultimat statement, and if you go for something like this, keep the rest of the outfit simple.Black ankle boots, and a white turtleneck work just fine. You can easily wear a vintage outfit of all denim, and cover it with a simple rain coat. Make sure the pieces you choose are in a variety of blues; light wash button down, and dark wash jeans for example.

Just because it’s rainy weather doesn’t mean you can’t wear a super girly item. A vintage baby doll dress in a unique pattern like polka dots can be matched with knee-high socks or tights and a pair of ankle boots.

You can also go for the baby doll look in a darker way. A black, corduroy dress with a patterned blouse underneath is a noticeable style, and paired with the right accessories is a big statement.

Of course, maybe you prefer your jacket do all the talking. Stick with a simple shirt and jeans underneath and pair it with a bright colored jacket in yellow.