9 Best Waterproof Boots for Men | Work Boots, Hiking Boots, Chelsea, Casual, Dressy

Finding the best waterproof boots — especially ones that look good — is challenging.
They’re typically made with comically thick lugs, too much rubber, and an outdoorsy design that’s more practical than stylish, but in this list, we’re giving you a balance of the best waterproof boots that excel in form and function.

I’ve put nine boots to the test to see if they hold up being submerged in water so you can have dry feet even on the rainiest days.

Our Waterproof Boot Buying Guide

1. Best Waterproof Work Boot: Irish Setter Wingshooter S.T. ($240)
2. Best Work Boot (that’s likely in stock): Brunt Marin Boot ($155)
3. Best Waterproof Chelsea: Ariat Wexford ($210)
4. Dressiest Waterproof Boot: Allen Edmonds Higgen’s Mill ($550)
5. The Classic: LL Bean Boot ($179)
6. Best Casual Waterproof Boot: Timberland 6’’ Premier (~$210)
7. Casual Winter Waterproof Boot: Anfibio Isak ($400)
8. Best Waterproof Hiking Boot: Danner Mountain 600 ($220)
9. Best Waterproof Heritage Boot: Red Wing 1907 Classic Moc Toe ($350)

The Best Waterproof Boots

To start, let’s look at two terrific waterproof work boots. Then we’ll move on to more city-friendly footwear that won’t look out of place in Manhattan — boots that withstand a lot of muck and grime while still being wearable for a nice dinner. 

I’ve tried to find something for a wide range of budgets and uses and even put a bonus Red Wing Heritage boot in there. (It isn’t waterproof, but it’s extra water resistant, and that’s enough for a lot of guys.)

1. Best Work Boot: Irish Setter’s Wingshooter S.T.

When people think of Irish Setter, they usually think of this boot or the Ashby line, but the Ashbies aren’t waterproof. (And don’t confuse this with the Wingshooter, a hunting boot. This is the Wingshooter S.T.)

It’s made with what they call an Ultradry system, which combines a lining made of synthetic membrane material with other waterproof components.

It’s also got a non-metallic safety toe that passes ASTM safety standards. The soles can withstand over 475 degrees and 18,000 volts of electricity. (The ASTM safety standard is 60 hertz for one minute under dry conditions.)

It’s one of the best looking I’ve ever seen for a legit work boot, and it’s even Goodyear welted — rare for a waterproof boot.

What I like:

• Waterproof membrane
• Meets ASTM Safety Standards for Electrical Hazards
• Goodyear leather welt
• $240

What I don’t like:

• This boot is so popular it often sells out.

2. Best Work Boot Runner-Up: Brunt Workwear Marin

I’ll give you two for the best work boots — this way, you’ve got options if one is sold out. (The runner-up is usually sold out. Get it together, guys!)

A great-value work boot is the Marin from Brunt Workwear. The most inexpensive boot on this list, it comes in at $135 (or an extra $10 if you need a safety toe), but it comes with stupendous waterproofing, with three layers to keep the elements out.

It’s also got a rubber-skinned sole with built-in oil and slip resistance. It’s made with lovely full-grain leather, and the combination of memory foam and rubber foam in its construction makes for terrific shock absorption.

Indeed, it’s not made with a Goodyear welt, so resoleing isn’t an option, but the price is right, and a bonus of the cemented construction is that it’s a remarkably flexible boot.

Less importantly but still nice to notice is that, unlike many waterproof work boots, this isn’t an especially bulky piece of footwear. It’s got heft, sure, but it fits much better with a casual streetwear outfit than other waterproof work boots you’re likely to find.

What I like:

• Can be converted from D to EE width
• Meets ASTM F2892-18 standards
• Comfortable
• $139 without the safety toe, $145 with the safety toe

What I don’t like:

• Not welted and not easily resoleable

3. Best Waterproof Chelsea: Ariat Wexford

The Ariat Wexford is one of the best-looking waterproof boots I own.  It’s sleek.  It’s not overbuilt and it comes in seven leathers (right now anyway), and while it looks like a traditional slip-on Chelsea boot, it’s got comfy cushioning in the insole that rebounds like a work boot. That means more comfort and less foot pain when spending all day on your feet.

Ariat waterproofs boots use their proprietary WaterProof Pro membrane, which is laminated to the leather uppers, and it’s built with a lightweight shank that provides extra stability — a useful feature as the boot ages.

This is one of the rare practical city boots that can easily transition to outdoor activities, and it’s pretty inexpensive at about $170. The reviews all say it’s great for farm work and rain, though if you’re ankle-deep in mud all day, you might want something taller without gussets.

What I like:

• Sleek, not overbuilt
• Comes in 7 leathers
• Very comfortable cushioning
• Waterproof membrane
• $210

What I don’t like:

• I’d like a taller gusseted tongue

4. Best Waterproof Dress Boot: Allen Edmonds Higgins Mill Weatherproof Boot

The nicest waterproof lace-up boot for men is Higgins Mill Weatherproof Boot, a sleek piece of work that fits just as well under business casual outfits as it does with jeans and a jacket.

The Higgins Mill is currently available in three weatherproof leathers — and they’re all made in the United States.

Allen Edmonds is an institution in the world of American footwear, and they spared no expense with the Chapman. It’s waterproof because of its waterproof membrane lining, hydrophobic leather, and storm welt.

That’s a kind of Goodyear welt that’s extra water resistant because of this lip that curves up onto the upper

It’s tough, grippy, and works with almost any outfit without seeming out of place. When I need to head to the office, but there’s a storm to brave, this is the boot.

It is the most expensive on the list at $550, but it’s justified by the laborious storm welt construction, high-quality leather, and the fact it’s made in America.

What I like:

• Classy enough to wear in town
• Rare storm welt combined with a waterproof membrane
• Available in 6 leathers and 2 styles, including a combat boot and a wing tip
• Made in America

What I don‘t like

• It’s bit pricey, if you’re not working in an office, maybe it’s not worth it.

5. Best Duck Boot: LL Bean Boot (The Bean Boot)

The best duck boot is the world-famous LL Bean duck boot, usually called The Bean Boot.

Here in New York City, this boot is absolutely everywhere whenever it rains. No one seems to have gotten the memo that regular Goodyear welts work fine in the rain, but hey, the Bean Boot is a classic that isn’t going anywhere.

The Bean Boot combines rubber bottoms with leather uppers: the rubber bottoms prevent water from entering the boot in the most exposed area to mud and wet.

In contrast, the leather uppers allow for some breathability. It’s an ingenious design and while it’s not made with a Goodyear welt, it is resoleable — if you’re willing to pay to send them back to LL Bean themselves, who are unsurprisingly specialized in the process.

Another cool aspect of the Bean Boot is that it comes in a variety of other iterations, like versions lined with flannel, chamois, Gore-Tex, and Thinsulate — there are even 10- and 12-inch high versions.

The main potential downsides are that it’s pretty loud — it’s not a subtle or urban boot, but it’s an American classic. Just makes sure you order the right size, as returns are torturous with this company. My sneaker size is 12, true size 11.5, and usual boot size is 11, but I had to order a 10.

What I like:

• Iconic and popular style
• Tons of variations available (eg. 8-inch, lined, insulated)
• $179
• Made in USA

What I don’t like:

• It’s very casual and not really my style

6. Best Casual Waterproof Boot: Timberland 6’’ Premium

Speaking of urban style, if someone new to New York asked for the best casual, urban, waterproof city boot for winter, they’d almost certainly be pointed to the Timberland 6-inch Premium Waterproof boot.

It really stands out because it’s such a cultural icon. It started out as a New England farming boot, but sales more than tripled in the 90s when it became a mainstay of hip-hop culture; catch them worn by Notorious BIG, Tupac, Jay-Z, and many other icons.

Described as “bonwelted,” this is a boot with seam-sealed waterproof construction, and it’s insulated as well, making it a favorite for cold nights in the Bronx or those early mornings of cow milking on your Massachusetts farm. (It’s a versatile boot!) Tucked beneath this nubuck leather is almost a pound of PrimaLoft insulation, and combined with the padded leather collar it retains heat in and has style in spades.

It is hard to keep clean but check out my video on cleaning them for tips on how to do that. The style isn’t for everyone (you won’t wear these to the office), but for most guys who just want something to wear around town when the weather is cold and wet, this boot works great.

What I like:

• PrimaLoft Insulation
• Padded leather collar
• $210

What I don’t like:

• A bit too casual for my taste.

7. Best Casual Boot Runner-Up: Anfibio’s Isak

If you want something similar to the Timberland but a bit sleeker and more refined — just a bit —  check out Anfibio’s Isak.

A less bulky and more rugged option, it’s made with waterproof materials and sealed stitches and seams, and it’s also insulated but with natural wool instead of synthetic PrimaLoft. This will appeal to guys who like natural materials: synthetic fabrics can sometimes get pretty stinky over time, and wool does a much better job of getting wet and drying without turning into a colony of bacteria.

Of course, those natural materials cost more, more than twice the price at $330, but they are made with better materials and in Canada to boot. (Timberlands are made in the Dominican Republic.)

What I like:

• Natural wool lining
• Rugged and sleek
• Side zip for easy on and off
• $400

What I don’t like

• The insulation makes it less versatile.

[SHOP THE ANFIBIO ISAK]

8. Best Waterproof Hiking Boot: Danner Mountain 600

The best waterproof hiking boot is the Danner Mountain 600. Danner is a brand with a reputation for making really durable hiking boots, and this one’s no exception.

They were one of the first traditional hiking boot companies to use GoreTex back in 1979 when it was hugely controversial to use synthetic materials in hiking boots. It’s similar to the hate some people have today about using poron and modern synthetic materials in heritage-style boots.

The Mountain 600 is more of a hybrid sneaker and boot than a traditional hiking boot. It has a 100% waterproof barrier, 200 grams of PrimaLoft insulation (half as much as the timberland), and EVA and Ortholite in the construction for shock absorption and comfort.

What’s also cool is it’s got Vibram’s Fuga Sole. Combined with the SPE midsole, it lets your foot expand to a wider surface while the lug pattern grips at multiple angles, providing stability when hiking on rocky ground.

What I like:

• Combines classic hiking boot style with modern materials
• Excellent traction from Vibram’s Fuga Sole
• $220

What I don’t like:

• Not easily resoleable

9. Best Waterproof Heritage Boot: Red WingClassic Moc Toe

The last entry is the best water resistant heritage boot, and I know I’m cheating a little here because Red Wing Heritage makes boots the old-fashioned way, so none of them are technically waterproof. You can’t make waterproof boots with late 19th-century or early 20th-century tech.

But the 1907 Classic Moc is their most waterproof heritage boot. Instead of the Goodyear welt, the 1907 hasa Norwegian-like storm welt, the most waterproof way to make an old-fashioned boot. It’s what jungle explorers used to wear a hundred years ago.

Now, there’s some debate about whether it’s a Norwegian welt or a Norwegian-like welt. It uses a single piece of leather that’s folded over and stitched to the upper and the midsole to keep water from getting inside the boot.
But it’s the most water resistant Red Wing Heritage boot you’ll find, plus it’s cool and old-fashioned and made in America with leather that’ll age beautifully — all the stuff most guys want from a cool, casual boot.

What I like:

• Norwegian-like welt, made to last, and resolable.
• Fantastic leathers, I think it looks great and is super casual.
• Great value at $310

What I don’t like:

• Psych, it’s water resistant, not waterproof, but good enough for my daily driver

Water Resistant vs Waterproof

There’s a difference between water-resistant and waterproofing technologies.
Often, guys erroneously think that a Goodyear welt (or its more water-resistant cousin, the storm welt) is waterproof, but that’s not the case.

Most great leather boots are made with a version of the resoleable Goodyear welt and they’re perfectly fine for walking in the rain or snow — and to be totally clear, that’s usually all the “waterproofness” the average person needs.

But sometimes people want waterproof boots, something you can wear standing in a creek or trudging around wet marshes.

Different companies have different standards for waterproofing, but here are some of the most popular methods:

Waterproof Lining

waterproof boots often have a lining inside the boot. It’s like a plastic bag but breathable, designed with tiny pores that are too small for water molecules to enter but large enough for warm air and water vapor to exit.

Back in the day, the only company making this sort of breathable waterproof membrane was GoreTex, but nowadays, a lot of companies have their proprietary waterproof membranes. To prevent leakage, the waterproof lining is laminated to the uppers, which seals the pores in the leather and the seams where the fabric is stitched together.

Cemented Waterproof Boots

Cemented waterproof boots are more common than welted waterproof boots. Boots like these are fairly low-tech: the upper is attached to the sole with an airtight method that prevents water from coming in through the seam between the upper and sole. Note that these kinds of boots don’t breathe as well as GoreTex.

Vulcanized Rubber

The other way to make waterproof boots is to use vulcanized rubber-like galoshes, rain boots, or LL Bean’s duck boots. The rubber isn’t very breathable and is more popular in temperate and cold climates like the US Midwest and East Coast.

The Downsides of Waterproof Boots

If you’re a heritage boot guy, you won’t often find welted waterproof boots because they’re made with modern materials and construction methods. The stitching isn’t waterproof when you make a welted boot, and seams will leak with prolonged wet exposure.

One downside of waterproof boots is that while they often use breathable materials, they’re not as breathable as normal leather because of the waterproof membrane or other waterproof materials and coatings.

There’s always a tradeoff between water resistance and breathability, and unless you need waterproof boots, most guys avoid them in warm weather.

But, if you live in wet and cold areas, waterproof boots are a solid investment.

Wrapping Up

I think I covered all the bases from somewhat dressy waterproof boots like the Allen Edmonds Chapman to something you can throw on and do yard work like the Marins.
Again, most people think they want waterproof boots, but something very water-resistant, like the Classic Moc, will keep your feet dry most of the time. But still, some people like to spend a lot of time out in the wet, and if you’re one of those guys, you’ve got what you need on this list.
Happy booting!