No matter what the season, a pair of waterproof leather boots should always be a part of your shoe rotation. They come in handy during spring showers or damp winters; buy a good pair and you’ll easily get a few years out of them.
During winters, a waterproof boot – with or without insulation – does a better job of blocking wind and the cold that comes along with it.
That being said, curating a list of such boots is easier said than done. They are distributed across so many sub-categories that it’s hard to fit all on a single buyer’s guide.
When buying a pair, it is important to pay attention to what the marketing tells you. It is easy to be misled by terms or phrases such as ‘treated with a water-resistant finish’ or ‘water-repellent’ and confuse it with water-proofing.
Water repellency might keep you dry in mildly damp conditions for a short period. But if you’re expecting a downpour or even the occasional splash of water, a waterproof boot is the way to go. Boots, by definition, are higher than low-cut shoes. Wearing them with a pair of water-repellent pants will keep you dry for longer.
When shopping online, look for literature that includes the word waterproof. This usually means that the leather used on the boot has a hydrophobic treatment and is also lined with a waterproof membrane.
There are different kinds of waterproof inner linings. Some brands use Gore-Tex. Others, like Cole Haan, Merrell, and Keen use in-house tech.
Next, you need to decide what do you need the boot for. Do you want a dressy pair for work, or a casual-wear boot for urban outings? On the other hand, if winter leather boots are what you’re after, then you’re going to be needing a lot more than mere waterproofing.
To make the process simple, we’ve split the guide into three boot categories:
A) Dress boots: These are sleek Chelsea, Lace-up, or Moc-toe silhouettes with low-profile outsoles that can be worn with business suits and dress pants. The sole and upper design differentiates a dress Chelsea Boot from a casual one. For example, casual boots like the Blundstone or Dr. Martens (the next category) have an aggressive outsole design with thicker leather uppers and work-boot trims.
B) Casual, work-boots, and athletic-inspired: This is a massive category that houses the widest range of waterproof leather boots. These versatile shoes are best used as casual wear and non-PPE work boots.
Some of the shoes have a casual-formal look to them and can pass off as office wear. Though some boots can be used as mild winter-wear, we recommend you take a look at our last category for products designed specifically for cold weather.
C) Winter boots: If you live in an area with sub-zero (below 0 C or 32 F) temperatures, then the shoe should not only be waterproof but insulated as well. The outsoles should either have soft, deep lugs for walking in the snow or be fitted with an anti-slip compound. A leather upper that is impervious to road salt is a bonus. Else, salt tends to chew up regular leather.
In our opinion, the following shoes represent the following categories the best. This alphabetically sorted list is a lengthy read; grab some coffee or a cup of whatever makes you happy.
Category 1: Waterproof leather dress boots
1) Clarks Men’s Tilden Zip II Waterproof
This is our affordable pick. The Tilden is a dressy and comfortable waterproof Chelsea boot at a sensible price.
A one-piece front and a side zipper add sleekness to the exterior. Inside, a cushioned footbed over a synthetic rubber sole adds cushioning and dependable traction.
2) Cole Haan Wagner Grand Apron Chukka Boot
This is a pricey shoe – no two ways about it. What you get in return is a high-end dress shoe with premium materials and rich detailing. Two pieces of quarter panels keep the side profile extremely clean; the folded lacing and collar edges give the Grand Apron Chukka a refined aesthetic.
A crimped midsole edge also adds to the formal design language. The midsole is, however, rubber instead of leather – that’s a plus for comfort and grip. The insole is leather-lined and padded for step-in cushioning.
This shoe also comes in a wide version that has more interior space.
Also see on Amazon: Cole Haan Wagner Grand Chelsea Boot
3) Cole Haan Wagner Grand Plain Toe Boot
With a Goodyear welted sole and classy leather lace-up silhouette, the Wagner Grand Plain Toe is the dressiest (and the most expensive) shoe in this section. The stitch-and-turn panels keep the unfinished edges out of sight and add design sophistication.
It’s also the only shoe here with a true leather sole – the rubber pods give the required traction and the latex footbed add some amount of cushioning. Due to the leather sole, the Wagner Grand Plain Toe isn’t as comfortable as shoes with rubber or Polyurethane outsoles.
But if a waterproof Dress shoe is what you want, this Cole Haan is the standard-bearer.
4) Ecco Vitrus III Gore-Tex Zip Boots
Ecco seldom disappoints. They are priced higher than the market median but consistently deliver quality products. Instead of fancy tech, Ecco focuses on quality ingredients that result in premium footwear.
There’s not a lot going on the Vitrus III’s upper. The use of large, soft leather panels keep the appearance low-key formal; the insides have a completely waterproof Gore-Tex membrane. The large side zippers make wearing and taking off the boot an easy task.
As with most Ecco shoes, the directly-injected Polyurethane midsole adds supportive cushioning and grip. There’s a leather-lined sockliner for step-in comfort.
Also see: Ecco Vitrus III Gore-Tex Chukka boot.
5) Johnston and Murphy XC4 Elkins Chelsea Boot
This shoe is our personal favorite in this category. The single panel forefoot gives this Chelsea boot a clean front profile and makes it suit-worthy. Mind you, we’re talking about the black leather version here. The blue tumbled leather variant, on the other hand, has a distinct casual shoe vibe.
The low-profile rubber outsole is cushioned and grips well over wet surfaces.
Also see on Amazon: Johnston and Murphy XC4 Hollis Chelsea Boot.
Category 2: Waterproof casual and work boots
2) Cole Haan Original Grand Boot
A low-top version of this shoe featured in our ‘comfortable dress shoe’ guide, but this version is waterproof with a different outsole. It’s amazing what a few design elements can do to the look of the shoe. The combination of raw stitching edges, metal eyelets, and lugged outsole gives it a rugged, outdoor-sey look.
It’s pretty functional too. The foam midsole adds plenty of cushioning for walking; the thermoplastic rubber outsole provides sufficient traction over most surfaces.
Also see on Amazon: Cole Haan Zerogrand Chelsea Boot
3) Danner Vertigo 917 Boot
Here’s another brand with beginnings in the work-boot industry that gradually crossed over to technical and hiking-inspired categories.
While Danner continues to produce work and tactical footwear, there are plenty of lifestyle boots. The Vertigo 917 is one of such.
The 917 modernizes the classic hiker silhouette by adding a Vibram outsole and EVA midsole along with a removable Ortholite footbed. But you know the real reason why the shoe is on this list. The leather upper is backed with a Gore-Tex membrane that keeps the water out.
If you’re looking for style, the 917 delivers with its rich full-grain leather upper and metallic D-rings. The upper fits snug, so try before you buy.
Also take a look at the Danner Mountain 600 – a narrow-fitting boot that is halfway between the 917 and the Mountain light – the 600’s classic styling is paired with a molded EVA Vibram midsole and outsole. The 600 is available with an Arctic Grip outsole – a compound that grips better on ice.
4) Dr. Marten’s Iowa Waterproof Boot
Most of Dr. Marten’s boots – including the winterized kind – are water-resistant and not waterproof. So the Iowa is the one you buy if you need a Doc that keeps the water out.
The Iowa also isn’t your typical Dr. Marten. It features a chunky sole that isn’t the same translucent kind as the originals, and it’s a high cut (vs. regular mid) along with ballistic Nylon tongue.
5) Ecco Turn Gore-Tex Chelsea Boot
If this Ecco shoe was built using smooth full-grain leather, it would have featured in our dress boot section. But it isn’t, and that’s what makes all the difference.
An oiled Nubuck leather and the elastic Gore add to the casual and almost work-wear vibe. A small Gore-Tex label is the only sign of the Ecco Turn’s waterproof capabilities.
Ecco directly injects a Polyurethane unisole to the welted upper for a strong, adhesive-free bond. As a cushioning material, Polyurethane foam is comfortable and weather resistant.
6) Keen Anchorage III Pull-on Waterproof Boots
One of the things that people love about Blundstones is their dual pull tab. Though a Blundstone features in our next section (winter boots), there’s a comfortable pull-on boot sold by Keen that happens to be comfortable, versatile, and waterproof.
Large pull tabs and the elastic Gore make putting the boots on a breeze; the roomy leather upper has a smooth interior fit. There’s a lot of midsole and outsole on the Anchorage. The Keen’s trademark kick-toe offers protection from the occasional bumps, and the sticky rubber lugs have plenty of traction.
The cushioning comes from the dual-density midsole and the specially-designed insole that also functions as a heat retention layer.
7) Sorel Madson Moc Toe Waterproof
There’s no other shoe on this guide in a Moccasin style, so here you go. The Sorel Madson features a classic faux-Moc toe on the soft yet waterproof Nubuck leather upper.
Unlike most of the boots listed here, the Madson’s midsole is made of cut-and-buff EVA – an excellent material for cushioning comfort. Underneath, a ribbed sheet of molded rubber gives you the grip you need.
8) Ugg Freamon Waterproof Chukka
If it weren’t for the lightweight foam unisole, the Freamon could have passed as a semi-dress shoe. The quarter panels are tucked into the soft, premium leather vamp to create a style with understated elegance. Two rows of lacing keep the panels close together, but only just.
This is our top pick if you’re looking for a waterproof and comfortable Chukka that is versatile enough for a variety of social settings.
Category 3: Leather winter boots
1) Blundstone 1392 Winter Chisel Toe
Just like Dr. Martens, the Blundstone began as a working-class staple out of Australia that turned into a fashion icon. The twin pull-tabs on a Chelsea Boot silhouette are an instantly recognizable feature.
If you’re wondering why we chose this particular Blundstone instead of classics such as the 510 or 1918, the answer lies in the 1392’s insulated upper and insole that works better for colder weather.
It’s worth underscoring that the upper insulation only covers the forward half of the interior; the rearfoot has a regular leather lining. There’s a lot of wool fleece insole insulating the bottom though.
As with most Blundstones, this style is unisex and available in sizes Women’s US 6 to Men’s US 12.
2) Kodiak Dundonald Arctic Grip Saltshield Boots
Road salt is excellent for traction on wintery days but bad for leather. Are you tired of the salt stains damaging your leather boots? This is your shoe; the Kodiak Dundonald is made of supple leather that is both water-proof and protects against winter salt.
That isn’t the long and short of it – not just yet. The midsole and outsole are made by Vibram, and the bottom has Arctic Ice lugs for better traction on wet ice and packed snow. It’s worth noting that the grip isn’t great on powdery snow or flaky ice – so it helps to temper expectations.
Because of its Thinsulate layer inside, the Dundonald is rated till minus 30 Celcius or -22 Fahrenheit. We tested this Kodiak boot in minus 10 Cel and -19 Windchill and it kept the foot warm and dry – with a caveat. As long as you’re walking, the feet stay warm. The problem begins once you stand still – the cold seeps in from the bottom. Not many boots pass this test, and the Kodiak is no exception.
By the way, the Kodiak brand is owned by Dickie’s workwear – a division that is a subsidiary of VF Corporation, the maker of Timberland, The North Face, Altra, Icebreaker, and Vans.
3) Merrell Ontario Thermo Mid Waterproof
This is the cold-weather version of the popular Merrell Ontario Mid waterproof. Along with an upper that keeps your feet dry, the leather has a salt-resistant treatment for those snowy conditions.
The leather upper is lined with Wool and Fleece for insulation during the winters, and so is the removable insole. And EVA-foam midsole makes the ride padded for hikes and urban commuting.
Just like the Kodiak Boot, this winterized Ontario mid is equipped with a Vibram Arctic Ice outsole.
4) Sorel Caribou Wool Boot
You thought you were going to be disappointed not to see a proper winter duck boot on this guide? Not so fast – we still have a couple of more boots to go.
Well, here you go. The Wool version of the Sorel Caribou is the boot for snowy winters. Though Sorel rates them at minus 40, we’ll take that with a pinch of salt. That said, this is a pretty handy, do-it-all boot for sub-zero temperatures.
The wool liner and the vulcanized shell under a waterproof leather upper work together to keep the cold, water, and road salt out. And if the inner bootie catches some slush, you can always take it out and wash them.
5) Ugg Men’s Hannen TL Boots
This classic silhouette is built using a smooth, premium leather, but the Hannen TL’s looks are more than skin-deep.
There’s wool everywhere. Inside, we mean. The waterproof leather lace-up is wool-lined for comfortable warmth during the cold months. Even the molded insole is wool-lined to keep the feet warm from below.
The EVA midsole serves a dual purpose. It provides all-day cushioning as well as insulation from the ground – the blown foam doesn’t transmit cold as readily as denser rubber soles.
Also see on Amazon: Ugg Seton TL Boot.