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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. A mix of sporty, casual and fancy is what Street style is all about, and rainy weather shouldn’t change that. 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.

Layer your look with a striped shirt topped with a knitted sweater shirt topped with a windbreaker jacket with simple jeans and a handbag. Here are some quick tips to keep in mind when dressing for rainy weather or dealing with unpredictable weather in general. 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. A gloomy day calls for bright and, more importantly, easy pieces. Grab the most vibrant stuff in your closet and experiment with color combos.
↓ 7 – Classy Coat for Rainy Winter Days
Fall is coming, and rainy days are coming with it. Today’s roundup is dedicated to guys’ looks for nasty fall weather, let’s see what to rock to feel comfy and look awesome. Wear a black and white striped dress with a white trench coat, red bag, and your choice of cute rain boots. One thing I like about the RAINS Jacket is that it’s stylish enough to wear around town even if it’s not raining.
It’s no surprise that when the heavens open, your outer layer is key. The first and most important rule in our rainy weather outfit guide is to have a decent waterproof coat or jacket. This is the ultimate clothing essential when it comes to building your rainy day look, especially as it’s the item that will first catch people’s eyes.
↓ 17 – Casual-Chic Street Style
Make sure the pieces you choose are in a variety of blues; light wash button down, and dark wash jeans for example. 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. Dark green pants with a simple t-shirt and button down look super trendy under a stylish wool jacket.
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. When autocomplete results are available use up and down arrows to review and enter to select.
Best casual outfits for when the rain falls in the autumn-winter season
For a more casual hipster outfit, it’s all about the layers. 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.
Getting a matching umbrella will make your outfit more beautiful on rainy days. Sometimes the simplest rainy day outfits are also the best. Look classy by wearing this elegant cream and black coat, light blue jeans, and brown rain boots. 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.
Find New Ways to Layer
Waterproof mascara is a must for rainy dates because you don’t want humidity ruining everything. Monsoon season is perhaps considered the most romantic season of all time. Despite all the mess and humidity, rain makes everything look so beautiful. The irony of this, however, is that I make an already dreary day even more bleak by dressing like I’ve just escaped from a cult compound.

If you have a loose, oversize shirt on top, stick with tighter skinny jeans on bottom. Whether it’s a summer downpour or a winter storm, fashion waits for nothing. Our rainy day outfits will ensure you’re looking fresh in any weather. Your favorite jeans are a cool and casual choice for a rainy day.
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. 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.
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. 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 for a see-through one which will pair well with anything.
Finish the look off with black ankle boots and a shoulder bag. 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!

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