4 Incredibly Stylish Rainy Day Outfits for Men

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William Barton Avatar by  William Barton | Last Updated:  Sep 03, 2020
4 Incredibly Stylish Rainy Day Outfits for Men

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.

Before we get into it, here’s a quick look at our favorite menswear brands for rainy day essentials.

Minimalist rain jackets
  • Weatherproof gear with a minimalist angle
  • Jackets, pants, ponchos, and bags available
  • Vast range of colorways
Water resistant jeans
  • Wind and weather-resistant denim
  • Styles available for many outdoors sports, from snowboarding to rock climbing
  • All styles feature a gusset and stretch fabric
Stylish outdoors gear
  • Outdoors clothes with water resistant coating
  • Stylish and modern, though not completely waterproof (good for when it might rain)
  • Portion of proceeds go to protect the American West wilderness
Modern galoshes
  • Galoshes for protecting your nice leather shoes
  • Range of other waterproof shoes and boots
  • Spiked and flat galoshes for different levels of grip (rain and snow)

You know what my favorite thing about rainy days is? 

When I show up for work with wet clothes and wet socks and sit in my chair for hours on end, wondering if I’m getting trench-foot. 

No.

I was born and raised in California, so for my first 27 years I saw it rain, like, three full times. But I moved to North Carolina where the summer storms are so intense, it makes you wonder whether you’ll drown if you stand outside. 

So I had to figure out my rainy day gear quick. And if you live somewhere like Portland where it’s always at least a little drizzly, lean in: here are five of my favorite rainy day outfits. 

Rainy Day Essentials

Going to work in the rain is just as much fun as getting teeth filled or spending your Christmas bonus on parking tickets. 

If it rains a lot in your part of the country, you’ll want to get a few solid basics that you can wear whenever it looks like it’ll be another grey, gloomy day. 

model wearing rains yellow waterproof jacket and everlane hat in the rain

These three rainy day essentials will do most of the heavy lifting in a downpour, so if you’re lacking proper rain gear, start here. 

#1: A Rain Jacket

Getting caught in the rain without a waterproof coat just sucks. Your shirt is soaking, you develop a funky smell—it’s no good.

The first thing in your rain wardrobe arsenal should be a jacket to keep your shoulders dry. It’s best to pick up a coat with a hood so you can keep your hair quaffed to perfection, even if the elements conspire against you. 

closeup of yellow rain jacket from rains

My favorite raincoat is the RAINS Jacket. It’s fully waterproof and has a hoodie with a bill for added protection. It’s lightweight and easy to roll up in a bag and take with me on the go. 

I picked mine up in the bright yellow, which I like—there aren’t many opportunities to wear this bright of a color and pull it off. A bright yellow rain jacket is appropriate and stylish even in winter, which can’t be said for other pieces of clothing. 

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RAINS makes a range of rainy day gear, from insulated jackets, to ponchos, to bags, to trousers. All of it is weatherproof and has a signature minimalist style to it that pairs well together and will fit easily into whatever wardrobe you have now.

A quick note on their sizing—they don’t have Small, Mediums, Or Large—they have Small/Medium, Medium/Large, Large/Extra-Large. I’m not sure why they do this, but I recommend choosing whichever is the smaller size. 

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I’m 6’1” 185lbs and I went with the Small/Medium jacket and it fits well—maybe even a little large in the shoulders. 

#2: Weatherproof Boots

I like the duck boot style for rainy days. They have a larger profile, so they don’t fit with tapered jeans, and you might struggle to get chinos to sit nicely over the top. 

Duck boots aren’t the fanciest shoes, and your work might not allow something so casual as part of the dress code

If you’re in a professional setting (law firm, accounting firm, etc.) consider a pair of galoshes. Galoshes are rubber liners you can slip over your leather shoes when the weather takes a turn for the worse. 

The concept is a little outdated, as you can find many storm-proof versions of your favorite style of shoe, but you may not want to invest a few hundred dollars into an extra pair just for rainy days. So that’s where SWIMS galoshes help. 

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SWIMS is the only brand I know of that has sleek, modern galoshes, and they carry a wide variety of colors. 

If you need to wear fancy shoes to the office, and you don’t want to buy a whole new weatherproof pair, SWIMS galoshes are an excellent middle ground. 

#3 Umbrella and Bag

I don’t need to explain why an umbrella is helpful in a rainstorm, right?

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I remember taking a trip to Dublin and trying to find the Guinness factory in the middle of an omnidirectional rainstorm. There were dozens of folded, shattered, maimed umbrellas packed into the trash cans. My takeaway? Get a solid umbrella. 

And if you’re a public transit commuter, it’s a relief to have a waterproof bag so you don’t have to worry about your laptop (or those important documents) soaking up any stray drops. 

RAINS also carries a large range of bags and backpacks—duffels, mountaineering packs, roll-tops, etc.—all water sealed with storm proof zippers. 

After seeing my bag (with everything I need to run my business) left out on the tarmac for 10 minutes in the middle of an Atlanta downpour while traveling, I’ll never travel without a waterproof bag again. Thankfully, I was using a waterproof bag then, too. 

Rainy Day in Summer, or Rainy Day in Winter?

We’re talking about two different beasts here. A rainy day in summer might just be a short blast, but a rainy day in winter might last a full week. 

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Depending on the season, your ideal rainy day outfit might need some added protection from the cold. 

Summer storms are relatively easy to dress for. I just carry my rain jacket in a bag if it looks like it might start coming down. If it does, I throw the jacket on and I’m good to go. 

One thing I like about the RAINS Jacket is that it’s stylish enough to wear around town even if it’s not raining. I won’t be wearing the bright yellow color unless it’s stormy outside, but other colorways like their navy and olive fit right into any casual wardrobe, even with blue skies above. 

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But in winter, it’s not so simple. One does not walk out into a New York winter with only a light coat.

So should you get two raincoats? One for warm months and one for cold months?

You could. But you don’t need to. 

Even though RAINS has several insulated puffer jackets and parkas, I chose a lighter jacket because I can always easily layer underneath. 

So if I’m visiting a cold climate in winter, I can still throw my rain jacket over my heavy wool coat.

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For that reason, I recommend a lighter rain jacket for most folks. That said, it may be worth investing in a winter-specific raincoat if your area has long, wet, and cold winters. 

4 Awesome Rainy Day Outfits for Guys

Outfit #1: Wet and Wild

I put together this first outfit for when it’s coming down, and it doesn’t look like it’ll let up soon. 

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I paired my yellow RAINS Jacket with the black RAINS Trousers. This outfit is waterproof (if you get the right shoes). Paired together, this jacket and trouser combo has a distinct casual vibe. 

What I like most about these trousers is that you can easily slip them on over whatever pants you’re wearing, so these are an excellent option if you take the train to work but don’t want to mess up your suit pants. 

The pockets of the trousers have storm-proof guards, so you can safely tuck your phone away no matter how hard it pours. 

The RAINS Jacket is just as easy to put over whatever you’ve got on, but I enjoy wearing it as a style piece. 

I went with the bright yellow, just because I loved it. But RAINS has nine other colorways available—some more toned down, some even more bodacious (like the space-man silver jacket). 

Outfit #2: Spring Downpour

This next outfit is for when it’s raining off and on. You don’t want to wear full on rain gear, but you don’t want to get soaking wet for lack of preparation. 

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I have a hoodie and raw denim jeans on (for great waterproof jeans, check out DUER). The raw denim is thick enough to keep my legs warm and mostly dry. Jeans can only protect you so much, and if it’s coming down in sheets, you’ll end up soaked no matter how thick the denim is. 

A baseball cap is always a nice touch for rainy days when doing your hair seems like an exercise in futility. If you’ve got curly hair like me, a cool cap like this one from Everlane is an easy way to keep your style boosted while avoiding a bad-hair day. 

On top of everything, I have the RAINS jacket. Again, it would be so easy to keep the jacket tucked in a backpack, and put it on when you need it. Or, you can rock it like I do here—the bright yellow is always appropriate in the rain. 

RAINS Jacket

My favorite raincoat. It’s fully waterproof and has a hoodie with a bill for added protection. It’s also lightweight and easy to roll up in a bag and take with me on the go. 

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Outfit #3: Outdoor Excursion

This is the outfit I wish I had when I took a group of students camping in Yosemite and we were caught in the middle of a 7-mile hike when it started raining about as hard as I’ve ever seen rain fall. 

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Duck boots are a must here (these are Sperry Topsider, though L.L. Bean makes their Bean Boots, which are also a great choice). The soles hold up well in the mud and they’re both warm and waterproof. 

On the bottom, I’ve got on a pair of Western Rise AT Slim pants. These are waterproof and have a gusset in the crotch, which is great for rock climbing or whenever you need to stretch out the legs a bit. 

I like that they’re tapered, but still have a wide enough leg opening to fit over my duck boots. On top I’ve got the Western Rise quilted coat, which is weather resistant (not waterproof like the RAINS coat, but will keep you dry if it’s sprinkling). 

Outfit #4: The Dapper Storm-Master

Just because it’s raining doesn’t mean you have to go all out with waterproof everything. 

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A suit is always appropriate, and there are a few ways to keep yourself dry enough to stay dapper looking. 

Make sure you’ve got an umbrella for this one, as a wool overcoat is warm, but doesn’t have the same water resistance you’ll find from technical fabrics.

Put a wool cap on top of this outfit to finish the look. 

This outfit is one of those situations where a pair of galoshes is a must. Come on, just look at those shoes—you wouldn’t want to ruin those beauties. 

Hoods Up

Whether it’s summer or winter, having a solid set of rain gear around is always a solid choice. Because you’ll only be wearing it a few times a month, your rain gear will last several years. So invest in high quality and an excellent fit. 

If you’re not up to laying down a few stacks on an entire wardrobe just for when it gets drizzly, check out RAINS. I’ve been loving their jacket, and it arrived just in time—it’s been raining for a week straight. 

Throw it on over your t-shirt in the warmer months, or over a wool coat in the winter. If you’re not sure whether it’ll rain, it tucks neatly into a bag so you can grab it when you need it.

RAINS

Minimalist at heart with a pinch of utility, RAINS will keep you dry with their waterproof and stylish jackets, pants, and bags.

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FAQs

What do you wear in rainy weather?

A waterproof jacket is the first priority. Waterproof shoes, or galoshes for whatever shoes you own now, are the second most important item. You can find great looking rain jackets at RAINS.

How can I look good on a rainy day?

If you pick up a few rainy day basics, you can make a variety of outfits that look fantastic. A bright yellow raincoat with a pair of jeans underneath is simple and looks great.

What do you wear when it’s raining and cold?

A waterproof jacket is the best thing you can wear when it’s raining and cold. Whatever you do, don’t get wet, as wet and cold combined is uncomfortable at best—dangerous at worst.