How to Style Men’s Rain Boots: Look Sharp and Bring on the Downpour

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by  Savarone Ammann | Last Updated: 

Can you be stylish and dry on a rainy day—or do you have to suck it up and pick one? We think you can be both.

Pick the right pair of sleek, minimal rain boots, cuff a good pair of pants, and combine them with a raincoat or umbrella and you’ve got a stylish fit that will keep the water out in a light drizzle or a full on rainstorm.

On hot days you can shed layers. On cold days you can bundle up. But on rainy days most guys just get caught off guard completely. 

The result?—soiled sneakers, soggy suede oxfords, drenched dress shoes, and clammy, wet feet for the rest of the day.

Most rain boots keep you bone dry but look ridiculously clunky with normal attire. Is it possible to properly style rain boots to enjoy protection from the rain, look stylish, and avoid showing up to the office looking like the captain of an industrial fishing vessel? 

Yes. Here’s how.

What You’ll Need to Style Men’s Rain Boots 

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When the rain is relentless and each puddle is an ominous black hole, here’s what you’ll need to get from A to B in style without getting soaked.

The most important factor is the right pair of rain boots. Once you’ve picked those out, you’ll need to identify which pants fit the best with them and how you can cuff or style your pants accordingly. From there, toss on a quality rain coat as a top layer or reach for a simple, black umbrella

  • Rain boots
  • Pants
  • Jacket or umbrella

Pick Your Rain Boots

Your rain boots need to be rugged, durable, and 100% waterproof. But, they don’t need to be clunky, cumbersome hunks of rubber with 12 additional materials, either. 

Your rain boots should keep water out but look slick and pair well with most of the pants in your closet. Here are two stellar options along with the best traits to look for in a stylish rain boot. 

SeaVees Bolinas Boot

Side angle of SeaVees Bolinas Boot

Beloved for their breezy walkaround sneakers, the SeaVees came out of left field and released the toughest, most stylish rain boot on the market.

Stylistically, the Bolinas Boot draws the sharp, minimal features of a Chelsea boot, but the thick, grippy outsole and rubber exterior give it the functionality of a working man’s boot. That’s a challenging mix of traits to pack into one piece of footwear.

SeaVees Bolinas Off Shore Boot

Stylistically, the Bolinas Boot draws the sharp, minimal features of a Chelsea boot, but the thick, grippy outsole and rubber exterior give it the functionality of a working man’s boot.

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On the outside, these boots are made from matte-finished, waterproof natural rubber with a thick grooved outsole for added traction. On the side, the Bolinas Boot offers a soft-knit lining that’ll keep your foot cozy while you trek through wet streets. 

Man standing in SeaVees Bolinas Boot

These boots only come in Military Olive, but this is the only color you’ll need for a pair of rain boots. It’s a smooth, dark, subdued shade of green that will pair with jeans, chinos, technical pants, and even high-end tapered sweats or joggers.

Some rain boots extend awkwardly up your shins. If you live in truly harsh climates and spend months out of the year sludging through knee-deep puddles and snow drifts, nough said. But the majority of us just need ankle-high boots that can keep a few inches of water at bay.

SeaVees picked the ideal length for the Bolinas Boot. They’ll fall right at the top of your ankle which will keep water out but not look clunky and miss-fitting with pants.

SeaVees Bolinas Off Shore Boot

Stylistically, the Bolinas Boot draws the sharp, minimal features of a Chelsea boot, but the thick, grippy outsole and rubber exterior give it the functionality of a working man’s boot.

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If you click this link and make a purchase, we earn a commission at no additional cost to you.

Huckberry All-Weather Duckboot

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Another excellent option for a worthy rain boot is Huckberry’s All-Weather Duckboot (AWD). This boot is marketed as a versatile, do-it-all option that will carry you from city streets to packed dirt trails and can be used during ski season, spring camping, or summer hiking.

The AWD is made from waterproof full-grain leather, with a Vibram rubber outsole, waxed laces, and brass hardware.

These boots come in black and brown. I think black is the clear winner, though, as it will pair better with all the pants in your closet and generally looks more understated and stylish. The brown model is really more of a tan than brown and exudes the style of a traditional East Coast rain boot or hunting boot over a boot you can style well.

These boots will sit above your ankle but avoid creeping too high up your shin which is great for outdoor treks and adventures. The AWD also offers a cushy, shock-absorbing insole that makes for a comfortable ride on or off-road.

All-Weather Duckboot

This versatile, do-it-all option will carry you from city streets to packed dirt trails and can be used during ski season, spring camping, or summer hiking.

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What to Look for in a Stylish Rain Boot

Top angle of SeaVees Bolinas Boot

When it comes to simple men’s style practices, less is often more. In the footwear department, that means getting all the functionality you need in the least amount of materials and bulk. 

If you’ve got long school-bus-yellow rain boots on, those will be the only thing noticeable about your fit. If you’ve got mid-cut, dark green rubber boots that fall just below a pair of cuffed chinos, you’ll enjoy similar waterproof protection without coming down from your level of daily style just because it’s raining out.

Since most stylish footwear like dress shoes, oxfords, wingtips, and dressier sneakers are a single color, aim to get rain boots in one, solid color too. This will make them appear less clunky and look more like your other, everyday footwear.

If you can, avoid chunky textures like rubber ridges around the shoe or big, heavy laces. So long as the material is fully waterproof, extra accents won’t keep the rain out any better but they will give your boots a utility look that you won’t need or want at the coffee shop or in the office.

SeaVees Bolinas Off Shore Boot

Stylistically, the Bolinas Boot draws the sharp, minimal features of a Chelsea boot, but the thick, grippy outsole and rubber exterior give it the functionality of a working man’s boot.

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If you click this link and make a purchase, we earn a commission at no additional cost to you.

Style Your Pants Accordingly

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Okay, you’ve got a nice pair of rain boots on deck. Now, which pants should you reach for, and how should you wear them? Because rain boots will generally sit higher than other footwear in your closet, you want to wear the shortest pair of pants you have with them. 

This doesn’t mean you want to show ankle or shin, though. As is the case with all your footwear, you want your pants to fall right above your shoes and avoid extra material bunching up at your ankles. 

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If your pants hang down over the boot and look scrunched up, then gently cuff them once or twice at the bottom to keep your rain boots uncovered and your pants nice and dry above the boots.

To keep your cuff looking clean and consistent, wear pants with a clear hem that will dictate the length of the cuff. Generally, a good cuff is about 1 to 1.5 thick.

Western Rise Evolution Pant

If you need a pair of pants that look great and you can wear it for a week straight without washing, the Evolution from Western Rise will get you there.

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Coat or Umbrella For Up Top

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With your rain boots on and your pants cleanly cuffed, you’ve taken care of your lower half. Now, you need to figure out how to keep your torso, arms, and head dry. You’ve got two options, a water-proof coat, preferably with a hood, or an umbrella.

What to Look for in a Raincoat

Model in taupe Everlane baseball hat and waterproof yellow jacket from rains

Picking stylish rain boots is much more important than picking a stylish rain jacket. Why? 

You can shed your jacket when you get to wherever you’re going and reveal a crisp, clean shirt underneath. If you kick off your shoes in the middle of a coffee shop, it’s not going to look so good.

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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So, favor durable materials that are fully waterproof. The last thing you want is pounding rain to seep through your jacket and into your shirt. I prefer a jacket with a hood so I can pull that thing up, maddash across the street, and get back inside without water droplets dribbling off my nose and into my morning coffee.

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Same with your rain boots, you want to pick a rain jacket in one, solid color that will pair seamlessly with everything. Again, school-bus-yellow is going to scream “school-bus-yellow”. 

One final note, pick a rain jacket with snug-fitting cuffs so water doesn’t sneak into baggy sleeves.

Choose an Umbrella, Instead

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If you don’t like the idea of buying a rain jacket and prefer to wear a purely stylish jacket, blazer, or shirt up top, then you’ll need an umbrella. 

Stick with a classic black umbrella. If you’re already dressed stylishly, you don’t need anyone to notice your fancy, high-tech umbrella. This should be a utility item that pops up, keeps you dry, then pops back closed and can be neatly tucked away.

Bring on the Downpour

Did you get a good idea for how you can throw together a rainy day fit that looks nearly as good as your regular fits?

Start with sleek, minimal rain boots composed of fully waterproof materials that offer a rugged, weather-proof edge. My pick is SeaVees Bolinas Boot.

SeaVees Bolinas Off Shore Boot

Stylistically, the Bolinas Boot draws the sharp, minimal features of a Chelsea boot, but the thick, grippy outsole and rubber exterior give it the functionality of a working man’s boot.

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If you click this link and make a purchase, we earn a commission at no additional cost to you.

Next, choose pants with a distinguished hem so you can easily cuff them as high as they need to go to sit right above your boots.

Lastly, keep your shirt pristine with a well-built rain jacket or umbrella and you’re ready to take on the day even when the weather app is wrong.

FAQs

What goes well with rain boots?

Stylish rain boots are fully waterproof, but still sleek and minimal where they can be. Pair your rain boots with cuffed pants and a rain jacket or umbrella.

Do guys wear rain boots?

Men’s rain boots can still be sleek, stylish, and effective in rainy weather. Check out SeaVees Bolinas Boot for the perfect hybrid between a boot that’s stylish but fully functional in the rain.

How do you style a rain boot?

If you can, opt for sleek, minimal, single-color rain boots that will keep water out but still look good with pants. Try cuffing your pants at the bottom so they don’t bunch up over your rain boots.

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