My Top 5 Picks for Best Boots for Upland Hunting [Tried and Tested]

Think of upland hunting as a game of endurance, not just accuracy. It’s like walking miles through damp grass, uneven terrain, and brush that goes up to the knees, hoping your dog locks up on scent. I’ve had hunts where my boots truly made the day, and hunts where they ruined it, too.

After years of chasing pheasants, quail, and grouse across rolling fields and thick covers, I’ve learned one lesson: your boots need to match your terrain, your season, and your stride. Some boots excel at early-season comfort, others at cold-weather durability. A few manage to do both.

I’ve personally tested or hunted alongside people who have worn each model on this list. Below, I’ll be sharing five of the best boots for upland hunting. Whether you hunt grassy prairies, rocky hillsides, or dew-soaked fields, there’s something here that will fit you easily. Let’s get started!

1) Danner Pronghorn

When I want one boot that can handle long miles, wet grass, and brush without killing my feet, I will always reach for the Danner Pronghorn. It’s built on a proven hunting platform, and comes with Gore-Tex lining, Vibram-style traction and a solid midsole support, perfect for people who are going on their first upland hunt.

It strikes an impressive balance between support and weight. In mixed upland country, it simply performs without drama. What really makes these boots shine is how effortlessly they transition from field to town. The design doesn’t scream “hunting boot,” which means I’ve often worn them casually without anyone noticing their true purpose.

The premium leather softens over time without losing structure, and the 8-inch height gives solid ankle support during long climbs. I’ve put these through rough terrain in the Dakotas, and they still look and perform as if they’ve got years left in them.

Pros

• It’s very supportive for long walks and uneven ground.
• Gore-Tex waterproofing keeps feet dry but breathable.
• Good out-of-the-box comfort, and lets you break in fast.
• Robust traction for varied terrain.

Cons

• Not the lightest boots on the market, heavier than some minimalist upland models.
• They’re pricey compared with budget options.
• If you need extreme insulation for deep-snow late-season hunts, this isn’t a heavy winter boot.

Why You Should Get It

I personally bought the Pronghorn because I wanted one reliable boot that I could use from late summer through early winter. For upland hunting, that means walking rugged, variable ground while carrying a light vest and dog treats, the Pronghorn’s support and waterproofing are perfect for that. The traction holds on damp grass, and the Gore-Tex keeps my socks dry without baking my feet on warm days. If you want one boot that does nearly everything well, this is my pick.

2) Danner Sharptail

The Sharptail is Danner’s upland-specific design, it’s lighter in feel than big mountain boots and tuned for the kind of short, fast, brushy hunting uplanders do. It’s a great compromise when you want leather durability and lower weight with modern comfort tech.

What really surprised me was how lightweight they felt despite their sturdy build. These boots are easy to lace, break in quickly, and stay comfortable for hours. The combination of classic craftsmanship and modern waterproof technology makes them a go-to for hunters who value both aesthetics and reliability. Over time, the leather ages beautifully, giving it a timeless patina that looks even better after a few seasons.

Pros

• It’s made specifically as an upland/brush boot.
• You’ll feel it’s way lighter and more agile than full mountain boots.
• It features Gore-Tex waterproofing and good breathability.
• Danner’s TerraForce platform gives it stability without adding extra weight.

Cons

• Less insulation for late-season snow than true winter boots.
• Rear-zip or snake versions add cost, choose based on your needs.
• If you need maximum ankle padding for heavy pack days, this is less cushioned than a tall Kenetrek.

Why You Should Get It

Sharptail is the boot I would pick if I’m doing fast walking through brush and need to move quietly and quickly. The build feels a lot more nimble than a big mountain boot, but it still resists briars and dampness thanks to the leather and Gore-Tex combo. If you want an upland-specific silhouette while going pheasant or woodcock hunting, this is the one I’d go for (and you should too).

3) Kenetrek Mountain Extreme 400

The Kenetrek Mountain Extreme 400 is for really serious hunters who tend to tackle steep, uneven upland terrain. I first wore these on a chukar hunt in Nevada, and it felt like strapping on actual armour on my feet. These boots are truly built like tanks, completely waterproof, insulated, and designed to handle punishment.

The 400-gram Thinsulate insulation kept my feet toasty even when the temperatures dropped below freezing. The first week, they felt a little bit stiff, but once they’re broken in, they become an absolute dream to deal with.

Want to know what stands out the most about them? It’s the support, no matter how rough the climb or descent is, your ankles will stay stable and protected. They’re heavier than standard upland boots, but that’s really the trade-off for the insane durability and traction they offer.

I’ve had mine for like 5 years now, and with occasional waxing, they still hold up like new.

Pros

• Unmatched ankle and arch support
• 400g Thinsulate insulation for cold weather
• Extremely durable and waterproof
• Great traction for rocky or mountainous uplands

Cons

• Requires a longer break-in period
• They’re a bit heavier than traditional upland boots

Why You Should Get It

If your upland hunts push into serious mountain terrain, Kenetrek’s Mountain Extreme is worth every penny. It’s supportive, bombproof, and nearly indestructible. I’ve crossed shale, scree, and brush with total stability. For serious hunters who want a boot that’ll last a decade, this is it.

4) Irish Setter Wingshooter

If there’s one boot that perfectly captures upland tradition, it has to be the Irish Setter Wingshooter. I remember buying these right before a late-season pheasant trip, drawn in by the classic moc-toe design and heritage look. But once I hit the field, it wasn’t just style that impressed me, it was actually sheer comfort.

What really surprised me was how lightweight they felt despite their sturdy build. These boots are easy to lace, break in quickly, and stay comfortable for hours. The combination of classic craftsmanship and modern waterproof technology makes them a go-to for hunters who value both aesthetics and reliability. Over time, the leather ages beautifully, giving them a timeless patina that looks even better after a few seasons.

Pros

• Waterproof and breathable Ultra Dry system
• Timeless moc-toe design
• Excellent arch and ankle support
• Great value for money

Cons

• Leather needs regular conditioning
• It’s not ideal for extremely rocky terrain

Why It’s Great for Upland Hunting

It’s perfect for classic bird hunts where you’re covering open ground. The waterproofing and comfort level make them ideal for cool, damp days in the field.

5) LaCrosse Uplander II

Some boots tend to feel old-fashioned, but maybe in a good way. The LaCrosse Uplander II is exactly one of those. They’re simple, sturdy, and fully waterproof. It’s the one I’d grab for early morning hunts when the fields are absolutely drenched.

I think the best part about them is how, when they say they’re waterproof, they actually mean it. The company doesn’t mess around, they just deliver what they’re told to deliver. Pair these boots with some of the best vests for upland hunting, and you’ve got yourself a master gear.

Pros

• 100% waterproof
• Rugged construction
• Wide, comfortable fit
• Great thorn resistance

Cons

• Heavy
• Stiff until broken in
• Less breathable

Why You Should Get It

The LaCrosse Uplander II isn’t fancy, but it’s one of the few boots I can wear through soaked grass and end the day with dry feet. Its wide fit means I can layer socks when it’s cold, and the waterproof bottom is bulletproof. This is the boot for hunters who face wet, unforgiving conditions.

My Personal Terrain-by-Terrain Picks

Buying and Care Guide for Upland Hunting Boots

If you really want your boots to last, you’re gonna have to care of them properly. In my years of hunting, I’ve taken great care of them. Let’s take a look at some of the tips that you might want to follow:

• Fit Comes First: Always try boots on at the end of the day when your feet are slightly swollen, remember that this is how they’ll feel after hours of walking. Also, always wear the socks you plan to hunt in.

• Break Them In Gradually: Even the best boots need time to conform to your feet. I wear mine around the house and even during short walks for a week or two before the season starts.

• Keep Them Clean: After each hunt, knock off mud and grass, wipe them down, and let them dry naturally. Then, condition your leather boots with a waterproofing wax or conditioner.

• Replace Insoles: Many hunters underestimate this. Swapping in a quality insole (like Superfeet or Danner’s orthotic insoles) can make old boots feel new and extend their life.

• Know When to Resole: High-end boots like Kenetrek, LaCrosse, and Danner can often be resoled. If the upper is still good, don’t toss them, instead, send it in for a rebuild.

Seasonal Boot Strategy

For each season, you will want to have a different pair of boots, whether it’s early season bird hunting in Michigan, or you’re going during late season, you need to pick a different pair. For example:

• Early Season (August to October): Go light, such as the Danner Sharptail or Irish Setter Wingshooter.
• Mid-season (October-November): Go for waterproof and cushioned shoes, such as Danner Pronghorn.
• Late Season (November-January): Have insulated and rugged shoes with you, such as the LaCrosse Uplander II.

What to Look for in Upland Hunting Boots

Before committing to any pair of upland hunting boots, it’s essential to know what separates a good boot from a great one. The right pair not only keeps your feet dry and supported but also enhances your mobility and endurance throughout the hunt. Here are a few things to look out for:

Comfort and Fit: A snug, secure fit that doesn’t pinch or slide is the foundation of a reliable boot. Too tight, and you risk blisters; too loose, and you’ll face instability on uneven ground. Look for a boot that fits well with your hunting socks, leaving just enough wiggle room for your toes.

Waterproofing: Whether you’re pushing through grass that has been soaked by the morning dew, or you’re crossing shallow streams, waterproofing is non-negotiable. Full-grain leather treated with waterproof membranes offers durability and dryness.

Support and Stability: Upland terrains can range from rocky ridges to muddy fields. High-ankle designs and reinforced midsoles prevent ankle rolls and reduce fatigue. Hunters who cover long distances should prioritise boots with responsive cushioning and arch support.

Traction and Outsoles: A reliable outsole makes all the difference in traction. Look for aggressive lug patterns that grip soil and grass without collecting debris. Vibram soles are a trusted choice among experienced hunters for their grip and longevity.

Material and Weight: Full-grain leather offers unmatched durability and weather resistance, while nylon or synthetic hybrids provide lighter weight and faster break-in times. Your ideal choice depends on whether you prioritise rugged protection or agile movement.

Break-in Tips for New Hunting Boots

No matter how advanced your boots are, they’ll need a proper break-in period before you take them on a long upland hunt. Skipping this step often leads to painful blisters, sore arches, and a ruined outing.

You should start by wearing your boots indoors for short periods of time to let the material adjust a bit to your foot’s natural shape. Then, increase the time, for example, wearing them on walks, short hikes, or while doing chores outdoors. This will allow the leather or fabric to flex and the insoles to mould comfortably.

If your boots are leather, apply a conditioner or softening oil to make them more pliable and resistant to cracking. For synthetic boots, you can speed up the process by wearing them with slightly thicker socks.

How to Match Your Boots to Hunting Terrain

Upland hunting isn’t really a one-size-fits-all sport. The right boot for an open prairie may fail miserably in marshy fields or rocky hillsides. Knowing how terrain influences performance will help you choose your upland gear technology strategically, here’s how:

Prairie and Grasslands: Lightweight boots with breathable uppers are ideal for covering miles in dry, flat terrain. You’ll want flexible soles that allow for natural movement and reduce fatigue during long chases.

Woodlands and Forests: In areas filled with fallen leaves, mud, and uneven ground, stability and waterproofing take priority. Go for a mid- to high-ankle design that keeps your footing secure and debris out.

Rocky or Mountainous Areas: These environments demand heavy-duty boots with rigid soles and excellent ankle support. Reinforced toe caps protect against stubs, while traction-heavy outsoles ensure grip on slippery slopes.

Wetlands or Marshes: Waterproof rubber or treated leather boots are your best allies here. Insulated liners will help if temperatures drop, and tall shafts prevent water or muck from seeping in.

Common Mistakes Hunters Make With Boots

Even experienced hunters tend to slip up when it comes to their footwear. Avoiding a few common mistakes can save you a world of discomfort. Here’s how:

1. Buying Boots Too Small or Too Big: Boots that fit perfectly in-store may feel different in the field once your feet swell from walking. Always try them on with the socks you’ll wear while hunting and aim for a snug-but-not-tight fit.
2. Ignoring Terrain Type: A lightweight upland boot might be great for dry fields but will underperform in soggy environments. Always choose your boots based on where you’ll hunt most frequently, not just on looks or brand reputation.
3. Neglecting Maintenance: Even the toughest boots need care. Failing to clean, dry, and condition your boots after hunts shortens their lifespan and compromises waterproofing.
4. Overlooking Insoles and Socks: Many hunters underestimate how much these two can affect comfort. The right combo can prevent blisters, regulate temperature, and reduce fatigue dramatically.
5. Not Replacing Worn-Out Gear: When soles wear down or waterproof membranes start leaking, it’s time for an upgrade. Holding onto damaged boots only leads to discomfort and performance issues.

Conclusion

If I could personally own only one pair, I’d go for the Danner Pronghorn again with hesitation. It’s comfortable, insanely waterproof, and versatile enough for everything from September quail to December pheasants.

For hunters that want to have lightweight agility, the Danner Sharptail takes the prize. If you’re on a budget you can go for the Irish Setter Wingshooter, they’ll surprise you.

If you’re the type to hunt in a rugged manner, the Kenetrek Mountain Extreme is unmatched.

Remember, it’s not only about the boots, it’s also about your technology, make sure to have the best apps for field tracking with you too!