What To Wear On A Rainy Day: The Must-Have Men’s Rain Gear We Recommend

by Barron Cuadro  |  in Style Tips

Trying to dress well, but it’s raining out? I hear ya. We’re covering the exact men’s rain gear that’s necessary to have if you want to stay dry while looking good. So if you’ve ever been unsure what to wear on a rainy day, this will serve as your guide.

Let’s face it: rain is a real buzzkill, especially when spring drags on, and you’re so close to summer weather but you’re still hit with the occasional rainy day. Sometimes we have to face a storm or two while still looking sharp.

I know you’re dying to whip out your shorts and short sleeve button-ups, but when rain’s on the forecast, this gear will make sure you’re prepared to beat it in style.

illustration of men in rain gear

The Weatherproof Wardrobe: What To Wear On A Rainy Day

So it’s too warm to wear full-on winter gear, but you still need to shield yourself from the elements. Here are some suggestions.

A weatherproof jacket

You have a few style options when it comes to your rainy day outerwear. What you choose will depend on your outfit’s level of formality.

In general, you can get away with having your coat or jacket at a higher level of formality than your outfit, but you can’t always wear a jacket that’s lower in formality than your outfit.

Quick example:

  • If you had jeans, an OCBD, and a sweater on… you can wear longer and more formal outerwear, like a trench or rain coat.
  • But if you were wearing a suit, you can’t throw on a short hooded zip-up jacket.

Make sense?

So you’ll want to familiarize yourself with the different types of coats available.

For a casual option, try a standard rain coat, anorak, or versatile lightweight parka. The key here is to make sure the jacket is designed to keep you dry in wet weather. Some features to look for:

  • water-resistant fabric (or fabric that’s been treated with a water-repellent coating)
  • sealed seams
  • storm placket and cuffs
  • flap pockets with fasteners
Barbour Ashby Wax Jacket
$395.00 $302.10
02/14/2023 01:03 pm GMT

A casual to smart casual option that is versatile enough to be worn with suits (for your wet office commute) would be the Barbour Border, Beaufort, or Ashby.

Barbours are not only waxed so they’re water resistant, the hem on these specific models should be long enough (on most guys) to cover your suit jacket, so it’s not an awkward look. Additionally, a Barbour over a suit is a classic high/low pairing that’s been around for decades.

Banana Republic Classic Trench Coat

Water resistant, classic relaxed cut, fully lined. You'll wear this for years.

Check Latest Price

Finally, your classic trench coat or rain coat is perfect for formal looks, like a suit and tie, but can easily be worn with any outfit that may be less formal.

The trench coat can come in a variety of lengths. If you’re of average height, a knee-length version should work just fine. Our friends at Gentleman’s Gazette cover everything you’d want to know about trench coats in their guide.

Boots or shoe covers

Similarly to the coat you choose, you want to make sure the shoes you’re wearing on a rainy day are built and designed to withstand wet weather.

My go-to rain boots are usually my L.L.Bean duck boots. I’ve worn these for a number of years. I also have a pair of weather-resistant Koio suede Chelsea boots that are extra lightweight and feature a lug sole. The design of these specific Chelseas lean more casual to smart casual.

L.L.Bean 8" Original Duck Boots

The legendary Maine-made Bean Boot – designed by "L.L." himself in 1912 and keeping feet dry and comfortable ever since. Chances are, you’ll only ever need one pair.

Shop L.L.Bean
Koio Chelsea Boots

Handsome, yet rugged winter-ready Chelsea boots.


If your style leans more rugged, you could also go with weather-resistant leather lace-up work boots. My favorite Chippewa 6″ Moc Toe boots are waterproof and feature a gusseted tongue that helps keep out any water and debris from entering the boot.

Need to wear dress shoes in the rain? I’d go with golashes or overshoes from SWIMS. They cover most of your leather dress shoe, and provides more than enough protection for your wet office commute.

And if the weather is particularly horrendous that day, SWIMS also makes an overboot that gives you full coverage.


If I’m just hanging out or running errands on rainy days, I prefer wearing a hat. That way I don’t have to worry about what my hair looks like after braving the elements outdoors.

The bucket hat has come in and out of style over the decades, and is currently back in. Historically, the original versions were made for rainy weather, and you can still wear them for the same purpose today.

A dressier option would be a wool fedora. These hats are water-repellent and can (somewhat) protect your hairstyle while keeping your head and part of your shoulders dry. Pair this hat with a serious rain coat or trench coat.

Polo Ralph Lauren Packable Bucket Hat

One of the original reasons for the bucket hat’s popularity was its ability to be folded down and stuffed in your pocket for later use. A lot of today’s bucket hats don’t hold up so well to this sort of treatment, but Polo Ralph Lauren’s Packable Bucket Hat specializes in it.

An interior pouch lets you fold the entire hat down into itself for easy storage, and its recycled polyester construction makes this bucket hat quick-drying and wrinkle resistant. Perfect for throwing in your backpack before you take a day trip.

Shop Ralph Lauren

And for the most casual of options, a standard baseball cap also works. If you’re going with a basic 5- or 6-panel brimmed hat, it most likely won’t be water-repellent, so you’ll need an umbrella. More on that next…


I prefer investing a tiny bit into a good umbrella, than just grabbing a cheapy at Wal-Mart which tends to break more easily.

The Shedrain WindPro compact vented umbrella has been my go-to. In my experience, no umbrella, vented or non-vented, is 100% flip-proof when the wind is strong enough. However, I’ve used this umbrella for years and haven’t had nearly as many issues as with my other umbrellas.

ShedRain also has an excellent lifetime warranty. I’ve had to contact the company twice to inquire about a repair—either the button mechanism became faulty, or one of the ribs snapped—and they often just send me a replacement.

Another option worth looking into is the AmazonBasics Automatic Travel Umbrella with Wind Vent. This umbrella has gotten surprisingly good reviews, especially considering its affordable price point. It also comes in a ton of colors.

And for a more luxurious and truly high quality umbrella, check out Fox Umbrella. They offer “solid” umbrellas, where the handle and stick are carved from one piece of solid wood. This can double as a walking stick. They also offer bespoke options. Pretty incredible.

Other Men’s Rain Gear You Need In Your Closet

Boot protector / waterproofer

I like to give my boots, especially the suede ones, an evenly coated mist of leather and suede protector. This, combined with brushing the nap to help get rid of any dirt and debris (before spraying) will help to keep the suede looking good and lengthen its life span.

We go into a few different ways to waterproof your leather shoes here. Number one is, obviously, to buy waterproof shoes, but beyond that, we’ve laid out other helpful tips.

wax, for your barbour

If you love a good waxed jacket like the Barbour we’ve mentioned above, eventually you’ll need to re-wax it.

Barbour Wax Thornproof Dressing
$26.00 ($3.85 / Ounce)

Can be used for any Barbour waxed jacket.

Check Latest Price
02/14/2023 08:03 am GMT

The Barbour site has a good guide on re-waxing and the steps you need to take.

shoe trees

The best way to extend the life of your leather shoes is to place shoe trees in them the second you get home, right after you take them off your feet.

Regularly wearing your shoes damages the leather over time. Think about it: excessive body heat, moisture, and creasing that forms as you walk around throughout the day all take a toll on the leather.

Shoe trees help to prevent all that potential damage by absorbing excess moisture and setting the shoe back to its original shape, minimizing any creases created from everyday use.

handkerchief / bandana

Finally, you may not have considered doing this before, but always carry a handkerchief or bandana in your back pocket.

Bandits Bandanas

Use code BARRONC15 for 15% off. Bandits partners up with artists to create exclusive, one-of-a-kind, limited-run bandanas. 10% goes to the charity of the artist's choice!

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I do this no matter the season; you never know when you’ll need to wipe something down, clean something up, or (most likely) wash your hands in a public restroom, only to realize there are no paper towels.

When it’s pouring during your commute, you may need to dry off your hands and face a bit once you arrive. Maybe you want to wipe down your bag or shoes. These bandanas / handkerchiefs always come in handy!

Now you’re prepared for a Rainy day With All The Right Rain Gear

Having to travel from place to place in the rain is never fun. Your clothes get wet, you unknowingly step in puddles that are deeper than they look, and your hair gets messed up from the moisture and wind, all before you arrive at your destination.

While we can’t always avoid being outside in the rain, we can prepare ourselves as much as possible so we don’t get completely soaked.

Do you carry some of these items with you on a rainy day? What else do you think is absolutely essential to bring along? Hit me up on Instagram if there’s something we should add to this list.