18 Pairs of Waterproof Shoes That’ll Keep Your Feet Dry No Matter Where You Are

We love a rainy day — when we can properly protect ourselves and show off our favorite rain jacket and umbrella. But life and weather patterns don’t always work out the way we hope and it usually involves the realization that you may now be forced to spend a few hours in soaking wet socks. You don’t deserve it, bud. You do deserve the best waterproof shoes, though.

Waterproof shoes for men can be a stylish lifesaver in inclement weather, but they’re also convenient for water activities and summer nights on the beach. Footwear designs with water-repellent properties come in a variety of styles that allow you to switch it up regardless of the season. Whether you need a water-friendly sandal for the beach or something more durable for your hiking trip, you’re sure to find a pair of waterproof shoes for men that will keep your feet dry and your style fire.

To help you get through those rainy commutes or give yourself some extra protection on your next outdoor adventure, SPY picked 18 pairs of waterproof shoes for men that keep your feet dry, no matter what Mother Nature throws your way. 

1. Merrell Men’s Moab 2 GTX Hiking Shoe

BEST OVERALL

Merrell is known for durable hiking gear, so you can count on them when looking for a pair of waterproof shoes for men. The rugged-looking shoes are constructed of synthetic leather and mesh upper, with a GORE-TEX waterproof membrane that’ll keep your feet dry on the wettest days. This low-top hiking shoe also comes with several beneficial properties to keep your feet supported, like an air-cushioned heel, Vibram sole and abrasion-resistant toe cap.

2. On Cloud 5 Waterproof Shoe

RUNNER UP

No longer cut your workout days short due to bad weather with On Running’s Cloud 5 Waterproof shoe. It features a completely waterproof and windproof outer membrane, making it a great everyday shoe. The footwear is also made of sustainable materials and has reflective elements for easy visibility in low-light conditions.

3. SOREL Madson II Chukka Waterproof Boot

BEST CHUKKA

Behold: A chukka boot you’ll never have to chukka into the garbage. This beauty from SOREL looks professional enough to rock at your 9 am meeting but can take on the most unprofessional of environments like rain, snow and sleet. Therefore, you can stomp through the soggy city streets and never worry about getting your socks wet. Style is well represented here — along with comfort, due to this chukka’s EVA footbed.

4. Hunter Play Short Rain Boots

BEST RAIN BOOTS

Hunter’s Play Short Rain Boots are the only footwear you need to combat rainy days. These boots will last a lifetime, thanks to their 100% waterproof, durable, natural rubber construction. Unlike most rain boots, this pair is lightweight and has a comfy block heel making it easy to walk in. You can get a pair of short rain boots in navy, black, gray, red, blue and green.

5. The North Face Skagit Water Shoe

BEST WATER SHOE

Any guys who hate walking on the beach barefoot would do well to pick up a pair of The North Face Skagit Water Shoes. They’re lightweight and breathable, which will cause you to forget that you’re even wearing shoes during your water activities. The water shoes feature an EVA midsole drainage system that drains excess water and has a mono-mesh screen to prevent you from kicking debris into your shoe.

6. Bogs Sauvie Slip-On Boot

EDITOR’S PICK

If you’re the type to rock rainboots all day, do it in these slip-on boots from Bogs. They copy the Chelsea boot style, so they’re readily wearable no matter your office setting. The best part (aside from the waterproofness) is that the cushion is made to fight odors, so no unwanted scents will seep into your footbed.

7. Vessi Everyday Classic Shoe

MOST COMFORTABLE

Vessi’s Everyday Classic Shoe are soft, cozy and breathable but also offer Vessi’s Dyma-tex® waterproof technology, consisting of thousands of nano pores to keep water out and your feet dry. The best part of these bad boys is their sock-like fit and comfy design that supports your feet to help them feel relaxed all day long.

8. Samuel Hubbard Rainy Day Founder

BEST FOR THE OFFICE

The Rainy Day Founder is essentially a dress shoe that will keep your feet dry in adverse weather. They’re made with a full leather upper with a waterproof membrane and feature a Davos® Ice Sole with a super grip, giving you increased traction to prevent slipping. Plus, the waterproof dress shoes don’t stray far from comfort, thanks to its Hubbard comfort system that offers plenty of cushion and arch support.

9. Rockport Northfield Oxford

BEST OXFORD

These Rockport Oxfords can easily be worked into your office attire. Because they have a slightly more rugged look, they sort of take the classic office shoe to a much more cool realm. They feature Hydro-Shield waterproofing, a removable shock-absorbent underfoot cushioning and a durable rubber outsole that provides real grip.

11. The Original L.L.Bean Boot

BEST DUCK BOOTS

L.L.Bean unveiled the first pair of duck boots back in 1912, and they have been a necessity for men who typically work outdoors since. The full-grain leather boots are waterproof and are tough enough to withstand inclement weather from rain to snow. While these boots may not look the most comfortable, we can assure you that’s not true, given they have a uniquely shaped foot form to provide stability and long-lasting comfort. And we can’t forget about the boot’s steel shank offering support to your feet.

12. UGG Stenton Boot

BEST UGG

Waterproof UGGs that can pass as regular boots and look A1 in the office? You’re not dreaming. These are the coziest boots on the planet — no ifs, and’s or buts to that claim. They have the softest inside you’ll ever experience in an office shoe and genuinely feel like your favorite at-home slippers. Because they’re waterproof, your favorite fur-liners will never experience any uncomfortable damp moments during your commute, keeping you cozy at your desk all day long.

13. Keen Targhee III Open Toe Sandal

BEST SANDAL

Sometimes a man needs a pair of waterproof sandals, and that’s exactly where Keen Targhee III Open Toe Sandals come to the rescue. They feature a KEEN.ALL-TERRAIN rubber outsole that provides superior traction on any surface. These sandals are designed with a leather, waterproof strap system to secure your feet to its EVA footbed. 

14. L.L.Bean Stonington Boots

MOST RUGGED

A masculine, waterproof look you can sport in the office? Hell yeah. The Stonington boots are a worn-looking, rugged pair of waterproof leather boots that mock the comfort and flexibility of your favorite sneaker. While we do not suggest you run in these, we assure you that they’ll look tough on the floors of your office. They tie together well with your favorite pair of rolled jeans and a semi-casual button-down shirt.

16. Timberland Waterproof Ankle Boot

BEST TIMBERLANDS

Your favorite pair of tan Tims might look a little too construction worker-y in your average workplace. But if you’re trying to sneak inside and pull off the Timberland look, we suggest you sport these ankle boots in black. They’re dark enough that nobody’s going to look twice and ask why you’re wearing Timberlands in the office and will keep your feet more than dry for the entire commute there. It’s a risk, but one that’s well worth taking.

17. Adadila Men’s Classic Lace Loafer

BEST LOAFER

If you need an office shoe for rainy days, these breathable slip-on loafers from Adadila are a great option. They have the style of a classic penny loafer, but can unexpectedly go everywhere a rain boot can without getting ruined. Navy ain’t your style? No worries, these babies come in a few colors, so one will surely and effortlessly match your wardrobe.