Mens Keen Waterproof Hiking Shoes

When you pick a pair of KEEN waterproof hiking shoes, you’re choosing protection and comfort that matter on the trail. This guide helps you compare models so you can find the right balance of waterproofing, fit (especially toe box room), traction and durability for how you hike.

You’ll save time and avoid buying the wrong style for your feet and routes.

Top Picks

Selection Criteria

You want shoes that protect your feet and match how you hike. We focused on waterproof performance, fit (toe box width and overall volume), immediate comfort out of the box, outsole traction for mixed terrain, weight for day hikes, and long-term durability. Price and versatility matter too—if a shoe serves both daily wear and trail use, it’s more valuable for most people.

You’re looking at a rugged, comfortable hiking shoe that works almost everywhere — from muddy trails to weekend errands. It pairs waterproof leather and KEEN.DRY breathability with a roomy toe box and a removable footbed, so you can wear it all day without feeling cramped.

The outsole has aggressive lugs for grip, and the build is solid enough for light backpacking or daily wear. If you want dependable waterproof performance without hauling a heavy boot, this is a practical, easy-to-live-with choice.

What People Say

You’ll find most people praise the comfort and roomy fit, especially the toe box and heel support. Customers often highlight the waterproofing and traction on mixed terrain, though a few mention faster wear on insoles or heavy-tread areas after very long use. Overall the shoe is seen as dependable for day hikes and everyday wear.

Overall Sentiment: Positive

When To Use

Versatility

You can wear these for short hikes, daily walks, light trail work, or casual outings. They bridge the gap between a hiking boot and an everyday shoe, so you don’t need separate footwear for wet-weather errands and weekend trails.

Durability

The leather upper, toe guard and bruise plate add real toughness, and many buyers report long service life. A few users who put heavy, high-mileage wear on them did notice insole and outsole wear sooner than expected, so they’re best for regular hiking and daily use rather than extreme thru-hiking.

Comfort

You’ll notice the generous toe box and cushioned heel cradle right away. The shoe breaks in quickly and the removable footbed lets you adjust arch support if you need it, making it comfortable for long days on foot.

Water Resistance

KEEN.DRY membrane keeps water out while allowing vapor to escape, and the PFC-free DWR helps the leather repel moisture. Most users find them reliably waterproof for rain and puddles, though long-term waterproofing can decline with heavy wear.

Indoor/Outdoor Usability

Non-marking outsole and moderate tread make them fine for indoor use and rough outdoor terrain alike. Be aware that on very smooth wet surfaces some users have found them a bit slippery, so mind your footing indoors after heavy rain.

Key Benefits

• Reliable waterproofing with KEEN.DRY and quick-dry lining
• Roomy toe box that reduces pinch and allows natural toe splay
• Good traction from KEEN All-Terrain rubber and multi-direction lugs
• Supportive midsole and removable footbed for long days on your feet

Current Price: $159.99

Rating: 4.3 (total: 8228+)

Get Details

You’re looking at a dependable, everyday hiking shoe that handles wet weather without feeling like a heavy mountaineering boot. It mixes waterproof leather and the KEEN.DRY membrane with a roomy toe box and removable footbed, so you can tweak the fit or add custom insoles.

The all-terrain rubber outsole gives traction on muddy trails and rocky sections, while the mid-cut profile adds a bit of ankle support for uneven ground. It’s a solid pick if you want something that works for trail days, rainy commutes and weekend travel.

What People Say

You’ll notice most people praise how comfortable these feel right out of the box, especially the roomy toe area and arch support. Customers also point to dependable waterproofing and good traction on many trail surfaces.

A smaller group raises concerns about outsole slippage on very smooth wet stone and occasional adhesive or wear issues after heavy use.

Overall Sentiment: Positive

When To Use

Versatility

These shoes work as a go-to pair for short to medium hikes, rainy-day city wear, and travel. They sit between a hiking boot and a daily shoe so you can use one pair for multiple activities instead of packing separate footwear.

Durability

The leather upper and hardened toe guard give the shoe a rugged feel and many buyers report long-lasting wear. There are occasional reports about adhesive or sole separation under very heavy use, so they’re best for regular hiking and day trips rather than extreme, high-mileage thru-hikes.

Comfort

You’ll notice the generous toe box and padded collar right away; the shoe breaks in quickly and the removable metatomical footbed provides good arch support. If you need extra support, swapping in a custom insole is straightforward.

Water Resistance

KEEN.DRY keeps water out while letting vapor escape, and the PFC-free DWR helps the leather shed moisture. Most users find them reliably waterproof for rain, puddles and stream crossings, though long-term performance depends on care and heavy wear.

Indoor/Outdoor Usability

The non-marking outsole and moderate tread make them fine for both indoor errands and outdoor trails. Be cautious on very smooth wet surfaces—some users found traction less secure on wet flagstone or slick concrete.

Key Benefits

• Reliable waterproofing with KEEN.DRY and moisture-wicking lining
• Roomy toe box and removable footbed for customizable comfort
• KEEN All-Terrain rubber outsole for grip on mixed surfaces
• Supportive midsole and mid-cut profile for stability on uneven ground

Current Price: $105.00

Rating: 4.3 (total: 4806+)

Get Details

You’ll find a hybrid that feels more like a sporty sneaker than a heavy boot, but still handles rough trail conditions. Leather upper plus KEEN.DRY waterproofing keeps things protected while the Contoured Fit follows your foot for a secure feel.

The outsole has multi-direction lugs for grip on loose dirt and roots, and the lightweight midsole cushioning keeps you moving without dragging you down. It’s a great pick if you want one pair for fast day hikes, rainy commutes and weekend trips — especially if you prefer a roomier, more forgiving fit.

What People Say

You’ll notice most buyers highlight how comfortable these shoes feel right away, especially if you need extra toe room or a wider fit. People also praise the waterproofing and the reliable feel on mixed trails, while a few mention the shoes can look bulky and that traction can be less secure on very smooth, wet stone.

Overall Sentiment: Positive

When To Use

Versatility

These sit neatly between a hiking shoe and a daily sneaker, so you can wear them for short to medium hikes, wet-weather city walking, and travel without needing a second pair for most outings.

Durability

The leather upper and tough rubber sole give a solid feel and many owners report good longevity for regular hiking and daily wear. There are occasional reports of outsole wear or adhesive issues under very heavy use, so they’re best for everyday trail use rather than extreme, high-mileage expeditions.

Comfort

You’ll notice the generous toe box and cushioned midsole right away; the Contoured Fit hugs the foot without pinching and the removable footbed makes it easy to add custom insoles if you want more support.

Water Resistance

KEEN.DRY keeps water out while letting sweat escape, and the treated leather sheds moisture. Most people find them reliably waterproof for rain, puddles and short stream crossings, with long-term performance helped by regular care.

Indoor/Outdoor Usability

The non-marking outsole and moderate tread make them fine for indoor errands and outdoor trails alike. Be mindful on very smooth, wet surfaces where traction can feel less secure compared with aggressive hiking soles.

Key Benefits

• Waterproof protection with KEEN.DRY membrane and water-resistant leather
• Roomy, contoured fit that accommodates wider feet and removable footbed
• High-traction rubber outsole with 4mm multi-direction lugs
• Lightweight cushioning and stability shank for confident, faster-paced hikes

Current Price: $144.99

Rating: 4.4 (total: 182+)

Get Details

You get a shoe that feels more like a tough, supportive sneaker than a heavy boot, which is great if you like to move freely on trails. The leather upper with KEEN.DRY waterproofing keeps puddles and light stream crossings out while still letting sweat escape, and the roomy toe box gives your toes space on long days.

Traction-focused outsoles handle muddy trails and rocky switchbacks, and the cushioned midsole plus a stability shank keeps you steady when the terrain gets uneven. It’s a solid all-rounder for rainy commutes, weekend hikes, and travel — a single pair you can wear around town and trust on an easy-to-moderate trail.

What People Say

You’ll notice most customers praise the comfortable fit—especially the roomy toe box—and consistent waterproofing. People commonly call out the grip and overall support for everyday hikes and yard or work use. A smaller number of buyers mention sizing quirks or occasional outsole wear and separation after heavy use, so a little care goes a long way.

Overall Sentiment: Positive

When To Use

Versatility

These sit between a sturdy hiking shoe and an everyday outdoor sneaker, so you can use them for wet-weather commutes, short to medium hikes, yard work and casual travel without swapping shoes for each activity.

Durability

The leather upper and robust rubber sole feel built to last for regular trail use; many owners report years of service. There are occasional reports of outsole separation or faster wear under very heavy use, so they’re best for typical hiking and daily wear rather than extreme, high-mileage use.

Comfort

You’ll notice the roomy toe box and cushioned collar right away. The contoured footbed and mesh lining help reduce hot spots, and the removable insole lets you add orthotics if you need them.

Water Resistance

KEEN.DRY keeps water out while allowing moisture to escape, and the treated leather sheds light rain and puddles. Most people find them reliably waterproof for wet trails and city weather.

Indoor/Outdoor Usability

Non-marking outsoles and a relatively tidy profile make them fine for indoor errands and outdoor trails alike. Watch for traction on very smooth, wet stone where aggressive hiking soles still have the edge.

Key Benefits

• Reliable waterproofing with KEEN.DRY membrane and durable leather upper
• Generous toe box and cushioned collar for all-day comfort
• High-traction, non-marking rubber outsole for mixed trail surfaces
• Stability shank and supportive midsole for uneven terrain

Current Price: $119.99

Rating: 4.2 (total: 10136+)

Get Details

You get a hiking shoe that feels broken-in from day one: lightweight enough to move freely but built solid where it counts. The KEEN.DRY membrane and treated upper keep puddles and damp trails from ruining your hike while the roomy toe box gives your toes space on long days.

The direct-attach construction and beefy rubber outsole mean these aren’t just comfortable — they’re meant to last and grip a variety of surfaces. Use them for wet-weather commutes, weekend trail walks, travel days when you want one reliable pair, or chores that demand solid traction; they’re a versatile, sensible pick if you want comfort and waterproofing without a heavy boot vibe.

What People Say

Most buyers appreciate the out-of-the-box comfort, roomy toe area, and dependable waterproofing. Customers frequently point to good traction and a solid build that holds up for everyday hikes and wet commutes.

A minority mention fit variations (some find them a touch roomy) or changes versus older models, so double-check sizing if you’re between sizes.

Overall Sentiment: Positive

When To Use

Versatility

These sit between a rugged trail shoe and an everyday outdoor sneaker, so you can use them for wet-weather commutes, short-to-medium hikes, yard work and travel without swapping shoes for each activity.

Durability

The fused upper, direct-attach construction and sturdy rubber sole give these a feel of long-lasting build quality; many owners report extended service. There are occasional notes about seam or insert wear under heavy use, so moderate maintenance will help extend their life.

Comfort

You’ll notice the roomy toe box and cushioned collar right away. The removable footbed supports arches and the breathable lining helps cut down hot spots, plus you can swap insoles if you use orthotics.

Water Resistance

KEEN.DRY waterproof membrane keeps external moisture out while allowing vapor to escape. For wet trails, puddles and light snow near ankle height, most users find them reliably water-resistant.

Indoor/Outdoor Usability

The non-marking outsole and tidy silhouette make these fine for indoor errands and outdoor trails alike. They handle mixed surfaces well, though very smooth wet stone can still be slippery for any hiking sole.

Key Benefits

• Reliable KEEN.DRY waterproofing that keeps feet dry while letting moisture escape
• Generous toe box and cushioned collar for comfortable, all-day wear
• KEEN.ALL-TERRAIN rubber outsole for confident grip on mud and rocks
• Direct-attach construction and durable materials for longer wear

Current Price: $169.95

Rating: 4.4 (total: 513+)

Get Details

You get a low-profile hiking shoe that handles wet trails and everyday wear with the kind of reliability you want when you’re out exploring. The KEEN.DRY waterproof membrane and treated leather upper keep puddles and damp grass from soaking your socks, while the grippy KEEN.ALL-TERRAIN outsole and 4mm lugs give confidence on muddy or rocky ground.

It’s light enough for travel days and long walks, tough enough for yard work and weekend hikes, and the roomy KEEN Original Fit means toes have space on longer outings. If you want a single pair that can do rainy commutes, casual trails and chores without feeling like a heavy boot, these are worth a look.

What People Say

Buyers often praise the dependable waterproofing and solid traction, and many notice the shoes feel stable and well built. Comfort gets mixed notes — plenty find the roomy toe box and support comfortable for long days, while some mention a break‑in period or fit differences between styles, so sizing can require a double-check.

Overall Sentiment: Positive

When To Use

Versatility

These shoes bridge trail performance and everyday practicality — you can wear them for wet-weather commutes, short-to-medium hikes, yard work and travel without swapping footwear for each task.

Durability

Durable leather, mesh reinforcement and a direct-feel rubber outsole give these a solid build; with basic care they hold up well to regular outdoor use, though heavy-duty wear may show seam or insert wear over time.

Comfort

You’ll appreciate the generous toe box and cushioned collar, plus a removable footbed if you want to swap in custom insoles. Some users note they’re a bit stiff at first but soften with wear.

Water Resistance

KEEN.DRY waterproof membrane keeps water out while allowing vapor to escape, so puddles and wet grass won’t soak your feet on typical outings.

Indoor/Outdoor Usability

The tidy silhouette and non-marking outsole make them fine for indoor errands and outdoor trails alike; they handle mixed surfaces well but very smooth wet stone can still be tricky for any outsole.

Key Benefits

• Reliable KEEN.DRY waterproofing that keeps external moisture out while allowing breathability
• KEEN.ALL-TERRAIN rubber outsole with 4mm multi-directional lugs for sure footing
• Roomy KEEN Original Fit and removable footbed for comfort and insole swaps
• Durable leather and mesh upper with treated DWR to protect the leather

Current Price: $140.00

Rating: 4.2 (total: 437+)

Get Details

FAQ

How Do These Shoes Fit And Should You Choose A Wide?

You’ll find KEEN men’s hiking shoes are built on a roomier last with a wider toe box than many running-style shoes, so many people report they run true to size. If you have naturally wide feet or like wiggle room at the toes for hiking, order the wide version or the next half size up and try them on with the socks you plan to hike in.

If you use custom orthotics, remove the factory insole to check volume before deciding. When buying online, try them on indoors and walk around; KEEN generally has a reasonable return window so you can confirm fit after a short break-in period.

Are Keen Men’s Targhee Waterproof Hiking Shoes Actually Waterproof And Breathable?

You can expect a waterproof membrane and waterproof leather on Targhee models that will keep your feet dry from puddles, damp trails, and regular rain, and the moisture-wicking lining plus Eco Anti-Odor tech helps reduce sweat smell. That said, they’re not designed for long periods of submersion or deep stream crossings, and waterproofing can lessen over years of heavy use.

Breathability is good for a waterproof shoe but you’ll still feel warmer and less ventilated than with a non-waterproof trail shoe. Practical care tip: dry them at room temperature after wet hikes, clean off mud, and reapply a PFC-free water repellent when the leather looks dry to keep the waterproofing effective.

How Durable Are The Soles And What Maintenance Or Tips Improve Longevity?

You’ll get a sturdy leather upper and rubber outsoles that perform well for day hikes and regular use, but high-mileage walkers have reported midsole or tread wear and occasional sole delamination over time. To extend life, rotate between shoes, clean off grit and mud after hikes, replace insoles when they compress, and recondition the leather periodically.

If the sole starts to lift mid-ride, a quality shoe adhesive like Shoe Goo can be a temporary fix, and for icy conditions add a traction device rather than relying on tread alone because some surfaces (wet flagstone, polished rock) can be slippery. Also give new shoes 20–50 miles of gradual break-in so seams and padding settle before you ask them to perform on a long trip.

What Customers Prefer

When choosing between the KEEN Targhee 3 WP, Targhee 3 Mid WP, and Hightrail Low WP, you usually weigh ankle support and protection versus weight and agility — the Mid gives extra ankle stability for rough, technical trails while the Low models are lighter and more nimble. You also prioritize waterproofing, comfort and outsole traction, so you’ll pick a Targhee for rugged durability and a cushioned fit and the Hightrail Low if you want a lighter, more breathable option that still keeps your feet dry.

Wrapping Up

If you want dependable, waterproof hiking shoes from KEEN, start by matching a model to how you hike. The Targhee 3 is the safe choice when you need a roomy toe box and reliable waterproof leather; it’s a strong all-rounder. Choose the Hightrail Low if you move fast on day hikes and prefer a sneaker-like feel with waterproof protection.

The older Targhee 2 is favored when rugged stability and a proven platform matter. The Targhee 4 is the pick if immediate comfort and modern construction are top priorities.

Finally, the Headout Low is a solid everyday waterproof option that handles yard work, commutes and trail use. Use fit and traction as your deciding factors: if your feet are wide, prioritize the roomier Targhee fits; if you hike steep, slippery trails, prioritize a model with aggressive outsole lugs.

You’ll get more enjoyment from every hike when the shoes match your feet and your routes.

This Roundup is reader-supported. When you click through links we may earn a referral commission on qualifying purchases.