What to Wear on Rainy Days Men

Rainy days are the worst, and it’s hard to be stylish when you’re stuck inside. We’ve compiled some tips for what to wear on rainy days, so you can still look good even if it’s pouring outside! Rainy days can make you feel like staying in bed all day, or hiding under your favorite blanket. But they don’t have to! Rainy days are perfect for staying in, but they’re also great opportunities to explore the world around you. Even if that just means exploring your own neighborhood! The key is to dress appropriately. In this article we’ll go over how to dress on rainy days so that you can stay warm and comfortable while still looking stylish.

What to Wear on Rainy Days Men

Rainy days are just another opportunity to look sharp.

You can wear a suit or you can wear jeans, but regardless of what you choose, it’s important to have the right accessories and even more important to know how to style them properly.

In this post, we’ll cover everything from what shoes you should be wearing (and when) to how to tie your scarf so that it doesn’t look like a giant triangle around your neck.

You’re a man. You have a job. You want to look good at work, but you also want to be comfortable.

So what do you do?

You wear a raincoat, of course!

Raincoats are great because they’re waterproof and they’ll keep you warm, but they also come with the added benefit of making you look like a badass. For example, if you’re out in the rain and someone asks you what kind of coat you’re wearing and why did chose that particular model, you can tell them all about it: “I really wanted [insert brand name] as my raincoat because [insert reason] but then I found out they discontinued it so I had to get this one instead.” They’ll think that’s cool, right?

Raincoats are great for men who want to look professional yet casual at the same time—which is basically everyone who wears them!

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The good news is that dressing for a rainy day is straightforward since you’re really only thinking of a few things: footwear, outerwear, and an umbrella. In addition, it helps that in one of classic style’s most influential nations, the UK, wet weather is all too common; the local tailoring tradition has long addressed the needs of men dressing for the wet weather. So, from experience, we have a considerable knowledge base on which to draw. If it’s the rainy shoulder season when cold weather hasn’t fully gone away but warm weather hasn’t yet arrived, a water-resistant overcoat is essential.

A classic trench coat is timeless
Are you ready for spring weather?

  1. Trench Coats
    If you’re wearing tailored clothes, the first overcoat to reach for is a classic khaki trench coat; this is an item with a storied history and iconic details that are designed specifically for wet weather. A proper trench coat features buckle straps on the sleeves, a stand collar with throat latch, and a back saddle, all intended to keep water away from your body. Similar to Sven Raphael Schneider, I think the most useful earmark of a trench may be storm pockets, which are made to enable you to carry small items without getting them wet. Even if you don’t use all of these features, they certainly look fantastic. Lastly, your trench coat is likely to be made of natural cotton gaberdine, a durable twill that provides water resistance without making use of fibers derived from plastics or petrochemicals.
  2. Raincoats
    An alternative to the trench is a regular raincoat. These tend to contain synthetic materials like nylon or polyester for water resistance, blended with cotton, so are less traditional in that sense. The advantage of a non-trench raincoat is that it is likely to be lightweight and packable and thus perfect for travel; you can compress the entire coat into a briefcase or weekender bag without wrinkling and whip it out when the skies begin to open up. Plain raincoats are also often minimalist in terms of design, having covered front buttons and no belt. So if you want to present a clean contemporary look or emphasize what suit you’re wearing when you have the coat open, they’re a fantastic choice.

A raincoat with minimal design features enables the rest of your outfit to stand out.
A raincoat with minimal design features enables the rest of your outfit to stand out.
Raincoats also come in reversible versions, with one side navy and the other khaki for versatility. This gives you a good set of inner pockets as well. I have an entirely navy blue variant that is lightweight wool on one side and a waterproof synthetic on the other. I wear a more elegant fabric side out until it starts to rain, at which point I just flip to the impermeable side.

  1. Casual Jackets
    Recently, there has been a movement toward some hybridization in the form of wearing casual outerwear, such as a waxed cotton canvas field jacket, over smart casual clothing like a sports coat, tie and OCBD, or instead of a sport coat. If you’re strolling in a country garden or visiting a historic house on a rainy weekend, this is a great option. The wax treatment gives these jackets an appealing sheen and the fabric itself is both rugged and natural. Some of the most well-known makers are Private White and Barbour, both British companies. The Barbour Beaufort and Sapper models seem to lend themselves best to accompanying more formal clothing while translating easily to completely casual wear.

If you do go with casual rainwear, try it first to see if it works with whatever tailoring you want to wear; something like an Australian oilskin duster would certainly be effective but incongruous. The same applies to things like Gore-Tex windbreakers and generic parkas. These will keep you dry but aren’t specific to a classic style aesthetic, so we won’t address them here.

  1. Performance Fabrics
    The technological innovations that have shaped 21st-century society have not passed over the menswear industry. A recent innovation is Loro Piana’s Storm System fabric, where wool and cashmere are made windproof and waterproof. though still breathable, through the application of an “extremely light micromolecular and microporous absorbent membrane.” This can be made not only into overcoats but into sport coats that you can wear alone when the weather is wet but that chilly.

Loro Piana’s Storm System fabric in the form of a sports coat.
Loro Piana’s Storm System fabric in the form of a sports coat. [Image Credit: Loro Piana (L)]
Shoes and Shoe Care for Rainy Weather
If you get caught without an overcoat and don’t have an umbrella, a damp suit will usually dry out just fine if you hang it properly and don’t expose it to strong heat in the drying process. However, soaked leather shoes are another story. Stories abound online of shoes that have been irreparably damaged due to rain. So, how do you prevent this?

As with many gentlemanly pursuits from ironing to setting a handkerchief just right in your breast pocket, preparation is the key. Check the weather forecast and choose your approach to footwear accordingly.

  1. Pre-Treating Your Shoes
    When rain is light or occasional, you can still wear your regular calf leather shoes with a natural oil-based sole treatment like Saphir’s Medaille d’Or Sole Guard. You apply this to the leather soles of your dress shoes and after it dries, it helps prevent water from permeating the shoe through the underside. The fact is that most shoe damage occurs from water wicking its way up through the sole and warping the leather, so, again, preparing ahead of time is the key.

A natural oil-based sole treatment helps prevent water permeating the shoe.
A natural oil-based sole treatment helps prevent water from permeating the shoe. [Image Credit: Saphir]
If you know rain is in the forecast, as a rule, you would also generally forego wearing suede or nubuck shoes, which are particularly prone to water damage. However, with another Saphir product, the Super Invulner Waterproofing Spray, you don’t need to. With an application of the spray perhaps every month or so, depending on use, water should run right off of suede. What’s more, along with the Sole Guard, these treatments provide stain and salt resistance in addition to waterproofing.

Shoe waterproofing
A Super Invulner is an easy yet effective way to protect your leather accessories from water and salt damage.

  1. Dress Shoes with Rubber Soles
    If you’re simply not into keeping up with treating your shoes, a step up in terms of protection that requires no maintenance is to buy some dress shoes with soles made of Dainite or an equivalent rubber. These are not the same rubber soles that appear on cheap shoes from Cole Haan or Kenneth Cole, which wear out quickly and are difficult to repair. Rather, these are durable, impenetrable, and slip-resistant and are used by high-end makers. Anyone who has worn shoes with leather soles knows the experience of slipping on a few droplets of water on a supermarket or office floor; with rubber soles, this annoying and embarrassing occurrence is a thing of the past. Dainite has long been a godsend for dress boots and is becoming more popular with dress shoes as well, such as those by Allen Edmonds. Crockett & Jones has a proprietary version developed in partnership with the Harborough Rubber Co. as part of their “city sole” range, first released in 2016.
  1. Overshoes or Galoshes
    When it’s raining cats and dogs, you may need sacrifice style points in favor of wearing utilitarian rain shoes or galoshes. The French galoche, which originally meant a wooden last for shaping shoes, later referred to wooden clogs and, more recently, to overshoes made in rubber. If you visit a historic house like the Bronte Parsonage Museum or the Bata Shoe Museum, you’ll see examples of overshoe that go back at least to the early 19th century.

For some reason, rubber galoshes or overshoes seem less common these days than a generation or two ago, either because men are becoming more indifferent to protecting already low-quality shoes or because men simply find these “shoe condoms” ugly. The fact is, galoshes will never look terrific; they add thickness and bulk to your feet, but, at the same time, they’re light and portable while providing optimal protection for your shoe investment. You can leave a pair in your briefcase, in the car, or in a drawer at the office. Galoshes should be thought of as a functional item more than an aesthetic choice if you choose to buy them.

Perhaps some men are put off by the cheap black rubber versions that are available in any shoe repair shop. These can be notoriously difficult to slip on and take off and can tear through in one season. You might as well tie plastic shopping bags over your shoes (which I have done in a pinch). However, as part of the revival of interest in menswear, some innovative companies have taken the lead and designed better galoshes. One of these is a Norwegian company called SWIMS, which makes them in multiple colors beyond the usual black.

SWIMS galoshes in brown
The appeal of SWIMS overshoes is not just the color choice–you can match your shoes or get a standout shade–but also how easily they go on and off while staying firmly in place when you want them to be. They come with a carrying bag as well, but at a price tag of $95. A disadvantage that they and most overshoe designs is that they leave the facing, where the laces are, uncovered. Another Scandinavian company, Fred & Matt from Sweden, has galoshes that are made of a handsewn, breathable material that cover your entire shoe. This eliminates the issue of other galoshes, including SWIMS, of leaving the area of the laces exposed to the elements. However, the range of colors is more limited–only the nondescript black will work with classic style–and the price is higher at $145. Both brands are positively reviewed online.

  1. Rain Boots
    Lastly, you can abandon all pretense of elegance and simply wear some sort of rain boot. You then carry your dress shoes in your briefcase or keep a pair at the office to change into. Rain shoes from L.L. Bean seem to be a popular choice in the US. I personally find them unattractive with tailored clothing, but you could say that you’re emulating the sprezzatura of Gianni Agnelli by wearing boots with a suit. They are made in shades of brown, so they kind of pair with the staple menswear colors, like gray and blue, if only in terms of color and not aesthetics. On the other hand, you may be able to track down something less likely to catch the eye; ultimately, you need to think of these as primarily functional items.

Hespokestyle’s Brian Sacawa wearing L.L. Bean “duck shoes” in rainy weather.
When I visit the UK, I like to do a bit of country walking, and I still like to wear a sports coat (perhaps a tweed jacket) and maybe a casual tie, so my rain boot of choice is a Wellington or “wellie.” These actually pair quite nicely with tailoring, as they are part of traditional British hunting attire and make you look something like a proper country gent. Obviously, they aren’t as portable as shorter galoshes, but a definite benefit is their height: you can tuck your trousers into them and dance in a muddy puddle with no need to visit the dry cleaners afterward. You’ll see a ton of them worn everywhere too, albeit mostly with more casual outdoor wear, so they don’t look out of place. You could try the look outside the UK too, but, following the rule of dressing for the environment, you likely would not wear these with tailoring in the city unless you’re Nick Wooster.

Nick Wooster wearing Wellington boots in NYC.
Nick Wooster wearing Wellington boots in NYC. [Image Credit: Maison Bentley Style]
The Debate on Shell Cordovan
When conditions are wet, many swear by shell cordovan shoes, even going to ridiculous extremes to test their response to water. Cordovan is special leather that is made from the flank leather of horses. However, for every testimonial trumpeting their water resistance, there is an equal number of horror stories about cordovan shoes developing persistent water spots after the slightest exposure to rain. The consensus seems to be that the resistance to damage depends on the cordovan and perhaps how it has been treated, so one shouldn’t view cordovans as specifically something to wear in the rain, especially considering that cordovan is usually far more costly than calf leather. Taking the usual precautions is the wisest approach.

Water damaged cordovan shoes on vcleat.
What to Do if Your Shoes are Soaked
Should your shoes get wet, whether their cordovan or other leather, the first priority is to dry them out, though gradually and in a way that doesn’t warp their original shape. Stuff the inside with crumpled newspaper and turn your shoes on their side to facilitate drying of the soles. Change the newspaper as it absorbs moisture and replace them with cedar shoe trees when the shoes are mostly dry. Whatever you do, avoid applying strong heat to the shoes. For instance, do not put them on a heating vent, as this will damage them. For water stains on the uppers of the shoe, try vigorous brushing with a horsehair shoe brush along with an appropriate cream or wax polish (non-turpentine for cordovan).

Lastly, though it’s not something you “wear” in wet weather, we would be remiss not to mention the primary accessory you need in the rain. First, when it looks like rain carry an umbrella, and make it a good one. All too often, out of laziness, lack of preparation or a sense of machismo, you’ll see well dressed gents walking (or running) in the rain without an umbrella. Others may prefer a portable $5 version from Duane Reade. However, the true gent appreciates a proper full-length umbrella with a curved wooden handle and a point, one that can double as a walking stick. Not surprisingly, some of the world’s top umbrella makers are based in the UK, such as Fox Umbrellas and James Smith and Co., whose shops are also worth a visit. There, the chance of rain is so omnipresent that a tightly rolled umbrella is virtually mandatory with morning wear at formal outdoor events. Italy boasts two historic umbrella makers as well, with Francesco Maglia in the north (Milan) and Mario Talarico in the south (Naples). Their solid-stick umbrellas with hand-steamed grips are truly a thing of beauty.

In the UK, a tightly rolled umbrella is a perfect utilitarian substitute for the walking stick of old.
Portability can be an issue, but the full-length umbrella is meant to be displayed, and the artisanal umbrella makers do sell short ones that still have beautiful handles. I personally have my eye on a packable version made by Fox Umbrellas, which combines the best of both worlds; it features a tip and handle that unscrew, allowing it to fit in your luggage.

Waterproof Men’s Leather Dress Gloves
When it is just above freezing, rain can be particulary cold on your hands. While leather dress gloves keep your hands warm and stylish, they are traditionally not a great option for wet weather. On the one hand, they absorb water and might make your hands feel even colder. On the other hand, you may end up with water stains on your gloves once you let them dry. Because of that, we designed a leather that is treated in a special way during the tanning process, thus repelling water. We call those leathers HydroPeccary, HydroNappa and HydroSuede and you can see a selection of classic men’s leather dress gloves in waterproof leathers in our shop here.

Dressing well doesn’t have to be only a fair weather proposition. With the proper preparation and protective clothing, you can laugh at storms and look good doing it. How do you dress on rainy days? What do you do in terms of your footwear when it’s wet outside? Tell us your approaches in the comments below.

What to Wear on Rainy Days to School

With the recent rain, it’s hard to know what to wear. We all want to look cute and keep our style, but we also don’t want to get soaked in the rain. Here are some tips for making sure your outfit is perfect for rainy days!

Rainy days can be a drag. From getting up in the morning to going to bed at night, you’re stuck in a dreary, cold world that makes you want to crawl under the covers and stay there until spring comes around again.

But you don’t have to! With these tips, you’ll learn how to dress for success on those rainy days—and make them more bearable.

As a student, you know that your school days can be long and tiresome. You’re tired of getting up early, tired of sitting in class all day, and tired of going home to do homework.

But one thing that can make it all worth it? The rain!

When it rains, you don’t have to worry about the sun beating down on your face or your hair turning frizzy from the humidity. All you have to do is throw on a raincoat and go outside to enjoy the fresh air and cool breeze that comes with the rain.

It’s a great time for some fun activities like running through puddles, catching some water drops in your mouth, or finding ways to stay dry while still having fun outside.

Where I’m living the weather is cold and rainy all fall and winter.
The only rain apparel I have is a super baggy raincoat that looks like I’m wearing a Niagara Falls Maid-of-the-Mist inspired plastic poncho!!! I’m concerned about coming across as childish, as I associate rain-gear with cutesy, matching brightly coloured rubber outfits for kids.
How can I keep warm, dry AND stylish?

While rain gear can certainly look unfashionable, there are still plenty of chic rain-proof options that won’t make you feel like a kid! The key is to think of rain gear the same way you think about other clothing.

We’ve already covered some school outfits that are cute and functional, so you can check those out for simple ideas. Then, when finding outfits for rainy days, keep in mind the same guidelines for fit and style that you use when shopping for non-rain clothes.

Also, be sure to choose rain gear that fits your personal style and that can be worn on a variety of different occasions. Most importantly, you should choose items that you feel good in; after all, when the weather is dreary, you’ll appreciate the extra pick-me-up that a stylish raincoat or sleek rain boots can give!

Keep scrolling to see my picks for what to wear on cold, rainy days. Below, I’ve created four rainy day outfits for school.

Rainy Day Outfits for School: Outfit #1
Rainy day outfits for school: Sheer navy blue floral long-sleeved blouse with ruffles across front and sleeves, black cropped relaxed-fit straight-leg pants with cuff, black camisole, adidas NEO Cloudfoam Advantage Stripe sneakers in white with black stripes, round black enamel disc earrings with clear stone at center and gold outlines, gold necklace with seven bezel-set clear stones, yellow raincoat with white-and-blue peony print and cinched waist, black pebbled tote with gold hardware
This look effortlessly combines casual and dressier pieces for a modern and trendy aesthetic and is a perfect outfit for cold, rainy days. It is also solid proof that you can pull off fun and colorful rain gear without looking like a kid!

To get it, begin by putting on a pretty navy blue floral blouse. Since the blouse is quite sheer, it’s a good idea to layer a black or navy camisole or tank top underneath, like the one shown here. Next, put on a pair of cool, relaxed-fit ankle-length pants, and add some chic Adidas sneakers.

Accessorize with deco-style stud earrings and a simple necklace for some subdued sparkle, and pick up a versatile black pebbled tote.

Lastly, mix things up with a bright and cheerful yellow floral print rain jacket that cinches at the waist; this detail is not only stylish but will help to create a more defined shape, so as to avoid a baggy, shapeless look. (For more on styling a piece like this, be sure to see our post on how to wear a raincoat.)

Rainy Day Outfits for School: Outfit #2
Light brown crewneck sweater with white alpaca with pink cheeks wearing a scarf, black wool elastic-waist skirt, beige lightweight rain coat with high neck, Burt’s Bees Tinted Lip Balm in
Tinted Lip Balm
Knee-High Boots
Since you say that you live in a place where it is cold and rainy all Fall and Winter long, it may be a good idea to invest in some slightly more expensive rain gear, including a timeless raincoat, like this one from Uniqlo (which, according to their website, is both rain- and wind-proof!), and a pair of high-quality and stylish rain boots. (Hunters are always a good bet.)

These pieces will keep you comfortable in the lousy weather and help you look stylish while doing so! They will also go with a wide variety of outfits, including dressier, more business-casual looks, like the one shown here.

To re-create the look for yourself, begin by putting on a neutral-colored sweater — I’m partial to this one, which features an adorable scarf-wearing llama! Next, put on a classy black wool skirt.

Add a pair of black opaque tights for warmth, and accessorize with some elegant purple stud earrings, a sophisticated gold bangle, and a black cross-body bag. Finally, grab a chic clear umbrella and swipe on some tinted lip balm, and you’re good to go!

Rainy Day Outfits for School: Outfit #3
Heather-gray fit-and-flare knit dress with three-quarter sleeves that flare out and are embroidered with burgundy, purple, and pale pink flowers; black glossy Chelsea-style rain boots, dark gray marled crew socks with cream-colored heels, toes, and tops with burgundy horizontal stripe; gold bow stud earrings with clear stones, gold necklace with faceted oval-shaped medium-green stone, dark gold bracelet with large gray stones and tiny green stones, black leggings, pale pink hooded rain jacket with cactus-print lining, black scalloped patent tote with pink, white, and green rose print and TED BAKER LONDON logo in gold
Ankle Boots
This easy-to-wear rainy day outfit is perfect for days when you feel like wearing something more feminine, but don’t feel like putting in a lot of time and effort.

To start, put on a sweet fit-and-flare dress with embroidered sleeves. Next, add some simple black leggings, as well as a pair of cozy marled socks and Chelsea-style rain boots. Scrunch down the socks so that they’re just peeking out over the tops of the boots for a stylish touch.

Accessorize with a pair of sparkly bow stud earrings, a green faceted pendant necklace, and a statement bracelet. Add a gorgeous patent floral-print scalloped tote, and put on a pale pink raincoat with a super-cute cactus-print lining to complete the look.

Rainy Day Outfits for School: Outfit #4
Red long-sleeved mock-neck swing sweater dress, purple hooded ultra-light parka, heather-charcoal and heather gray knit mittens, cognac-brown faux-leather backpack, cognac-brown and dark brown duck boots, gold

For days when the weather is really miserable, you’re going to need all of the warmth you can get, and this rainy day outfit for school delivers it in a way that is cheerful and colorful, and not at all dreary.

Put on a mock-neck sweater-dress in an uplifting shade of red, as well as a pair of light gray cable-knit tights. (These ones, from Uniqlo, feature their Heattech technology to keep you super warm.) Next, put on a fun gold “pom-pom” statement necklace for a little something unexpected.

Now for the functional pieces. Preppy duck boots will not only keep your feet nice and warm, but will also look great with a variety of different looks. A purple down parka will keep the bad weather at bay, while making for a nice change from the usual dark outerwear colors.

Finally, slip on a pair of cozy heather-gray mittens, and grab a stylish cognac-brown faux-leather backpack to finish off the ensemble.

Rainy Day Outfits for School: Outfit #5

Trench coat
Leather pants
Combat boots

A classic trench coat is a wardrobe staple and is perfect for keeping you dry — and stylish — on rainy days. For this cute outfit, we paired the trench with faux leather leggings, an oversized t-shirt, combat boots, and a glam gold watch. This outfit would look great on campus but could also be worn out to lunch with friends or even transition into the night.

I hope that these rainy day outfits for school have shown you how to dress for cold, rainy weather in a sleek and stylish way. Stay warm out there! Thanks for your question!

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Is there something in your closet that you want to wear but have no idea how to style? Do you need advice on what to wear to an upcoming event? Do you have a specific fashion conundrum?

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