Best waterproof leather boots for men

Regardless of the season, a pair of waterproof leather boots should always be a part of your shoe rotation. They are useful during spring showers and wet winters; buy a good pair and they’ll last for years.

During winter, a waterproof boot does a better job of blocking the wind and cold than regular boots.

That being said, there’s a difference between ‘treated with a water-resistant finish’ or ‘water-repellent’ and water-proofing that works in real-world conditions.

A water-repellent upper will briefly keep the feet dry during light rains. But if you’re going to be spending a lot of time in wet conditions, a waterproof upper (and sole) is what the shoe needs.

Boots, by definition, are higher than low-cut shoes. Wearing them with a pair of water-repellent pants will keep the feet dry for longer.

By the way, if you’re looking for quality water-repellent dress-casual pants, we highly recommend the dressy Theory Zaine Neoteric pant or the 7 For All Mankind Adrien tech-series pants in a casual 5-pocket style. An affordable option is the Perry Ellis Portfolio pant with a water-repellent finish and a slim dressy cut.

On a related note, we also reviewed the Eddie Bauer Guide Pro pants a while ago. These hiking pants have a water-repellent shell with an insulated fleece lining.

When shopping online, look for literature that includes the word waterproof. This means that the leather used on the boot has a hydrophobic treatment and is also lined with a waterproof membrane.

Gore-Tex is the gold standard of waterproof yet breathable membranes.

There are different kinds of waterproof inner linings. Some brands use Gore-Tex. Others, like Cole Haan and Johnston & Murphy, use other waterproofing technologies.

Next, we need to decide what occasion the boot is for. Is it 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 need more than just waterproofing.

To make the search process simple, we’ve grouped this guide into several categories:

A) Casual work boots and retro hikers: This category offers the widest range of waterproof leather boots. These versatile shoes are best used as casual wear and non-PPE work boots. The Timberland 6″ Premium and Dr Martens Iowa Tract II are good examples.

Some of the shoes have a casual-formal appearance and can pass off as office wear. The Timberland boot is also insulated, so it can be used during winter.

B) Dress boots: These are sleek Chelsea, Chukka, and lace-up silhouettes that can be paired with business casuals. On the other hand, if you’re looking for low-cut waterproof dress shoes, here’s our list of recommended shoes.

C) Winter boots: If you live in an area with sub-zero (below 0 C or 32 F) temperatures, then the shoe should be waterproof and insulated.

The outsoles should either have soft, deep lugs for walking in the snow or have anti-slip rubber. A leather upper that resists road salt is a bonus, as the salt tends to chew up non-treated leather.

Category 1: Waterproof work boots and retro hikers

1) Timberland Premium 6-Inch Waterproof Boot

The Timberland 6-inch boot needs no introduction. The large Nubuck leather panels, metal eyelets, and four-line stitch make it one of the most recognizable silhouettes in the industry.

Featured here is the waterproof version with an insulated interior. The heel collar and inner lining use 400 grams of Primaloft insulation – an effective substitute for natural down. This makes the 6-inch boot an excellent choice for damp winters.

The ride comfort comes from the cushioned removable insole and rubber sole. The deep outsole lugs are durable and grip well over most surfaces except for icy sidewalks.

2) Dr. Marten’s Iowa Tract II Waterproof Boot

Most of Dr. Marten’s boots – including the winterized kind – are water-resistant and not waterproof. So the Iowa Tract is the one you buy if you need a Doc M boot that keeps the water out. This has an 8-inch cut, thus making the Iowa Tract II a taller boot than the Timberland Premium 6-inch.

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 a ballistic Nylon tongue.

The upper uses the oiled ‘Crazy Horse’ material – an oil-pull leather that temporarily lightens when push your fingers under it.

Category 2: Waterproof leather dress boots

1) Allen Edmonds Higgins Mill Weatherproof

Calling the Allen Edmonds Higgins Mill a ‘dress boot’ is a bit odd, considering that this model is inspired by logging boots.

But in a world of sweatpants and smartwatches, the AE Higgins Mills boot is as dressy as it gets. The all-black in particular, is a dressy take on the Higgins.

There are two variants of the Higgins Mill – one with a leather sole and another with a rubber lug sole. Since we’re discussing waterproof boots, we recommend the rubber sole version due to its grip and water-repelling properties.

The upper uses a simple Derby construction with large, waterproof leather panels and waxed laces. A Goodyear storm welt connects the upper to the rubber sole, and that gives the Higgins Mill a classic dress boot aesthetic.

It is expensive, but then, this is a US-made boot with quality materials.

2) Cole Haan Originalgrand Chukka

This Chukka version of the Cole Haan Originalgrand has the same sole as the Originalgrand Oxford, but with a true-to-size upper and a waterproof lining.

The smooth leather panels are stitched together to result in a minimalist style that looks premium. There are comfort-oriented features like the padded tongue and soft foam ‘Achilles’ pod to prevent chafing.

Take note; the forefoot insole is not padded. This may pose a problem when replacing the stock insole with a thicker orthotic.

Only the heel and forefoot have outsole rubber inserts. The grip on wet surfaces could have been better.

A molded EVA foam insole and midsole makes the shoe cushioned and supportive enough for daily wear. If there’s one thing we’d like to see improved, that would be the outsole traction on wet and smooth surfaces.

3) Ecco ST1 Hybrid Chukka Gore-Tex

We have reviewed the low-cut version of the ST1 Hybrid GTX, and this dressy Chukka boot uses very similar materials and an identical sole unit.

The corrected-grain leather upper has a Gore-Tex membrane to keep the water out. Though this shoe lacks a gusset, the high-cut construction prevents moisture from entering. The secure upper fits true to size.

The ST1 Hybrid has a dual-density Polyurethane midsole with a soft heel core.

The ST1 Hybrid’s midsole uses Phorene – a PU foam variant that is relatively softer than standard PU soles.

The Ecco ST1 Hybrid boot uses a functional welt that’s stitched to the upper. The ride comfort and support are delivered by the Polyurethane midsole that Ecco calls ‘Phorene’. When combined with the cushy leather-lined insole, the ST1 offers excellent comfort for everyday wear.

The synthetic rubber outsole grips extremely well on damp surfaces, thus making it a true all-season shoe.

4) Johnston and Murphy XC4 Henson

The J&M Henson’s simple derby design blends elements from vintage combat footwear as well as modern work boots. A round-toe design and large quarter panels keep the aesthetics clean and also make the boot versatile from a styling perspective.

There’s plenty of comfort too; the smooth leather upper keeps the interiors smooth and easy to break in. The heel collar is soft and plushly padded to minimize Achilles irritation; the folded tongue flap helps prevent leather bite.

Instead of a traditional leather sole, the Johnston & Murphy Henson uses a dual-density midsole/outsole. There’s a firmer layer on top for stability, and a relatively softer base for cushioning comfort. Having a rubber sole also improves the grip on wet sidewalks while keeping moisture out.

Category 3: Leather winter boots

1) Blundstone BL566 Waterproof Winter Chelsea

Just like Dr. Martens, the Blundstone began as a working-class staple out of Australia that eventually became a fashion icon. The twin pull tabs on a Blundstone Chelsea boot are instantly recognizable from afar.

If you’re wondering why we chose this particular Blundstone instead of classics such as the 510 or 1918, the answer lies in the 566’s insulated upper and shearling footbed that delivers better performance during the cold and rainy months.

It’s worth underscoring that the Thinsulate insulation only covers the forward half of the interior; the rearfoot has a regular leather lining. As with most Blundstones, this style is unisex and available in sizes US 4 to US 13.

2) 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.

3) Sorel Caribou Wool Boot

You thought you were going to be disappointed not to see a proper winter duck boot on this guide?

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 dependable 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 it.