Men's Headout Mid Height Waterproof All Terrain Hiking Boot - Leather

Our review of the KEEN Men's Headout Mid Height Waterproof All Terrain Hiking Boot finds it best for outdoorsmen who want a durable, breathable boot with roomy toe space for long days on varied trails. The single biggest reason to buy is the combination of premium leather, breathable mesh lining and a waterproof KEEN.DRY membrane that keeps feet comfortable through wet and warm conditions without sacrificing protection. The boots are built on KEEN's wider Original Fit, so they suit walkers and hikers who prefer extra toe room and a stable platform for uneven terrain.

Key Features

• Durable materials: Premium leather and performance mesh provide abrasion resistance while still allowing the shoe to stay relatively lightweight for extended wear.
• Waterproof protection: The KEEN.DRY waterproof breathable membrane seals out rain and puddles while letting vapor escape to reduce clamminess on long outings.
• All-terrain traction: KEEN.ALL-TERRAIN rubber outsole with 4mm multidirectional lugs delivers confident grip on muddy trails and rocky surfaces.
• Supportive underfoot: A molded stability shank and shock-absorbing cushioning offer steadier foot placement and reduced fatigue on uneven ground.
• Easy on/off fit: The Speed Lace system creates a secure, adjustable fit quickly and keeps the boot convenient for frequent stops.
• Removable footbed: The included footbed with arch support can be removed for custom orthotics or cleaning to extend comfort life.

Who It's For

The Headout Mid is aimed at hikers, weekend trail users, and outdoor workers who need a waterproof mid-height boot with a roomier toe box and long-wear materials. Its combination of leather and mesh makes it a sensible choice for all-season use, from spring showers to cool fall hikes, and for anyone who values breathability alongside weather protection.

Those who demand very soft, flexible soles for technical scrambling or prefer a narrow racing fit should look elsewhere; some customers report an initially stiff sole and the wider KEEN Original Fit may feel too generous for narrow-footed users.

Pros & Cons

Pros

• Comfortable, roomy toe box that reduces hot spots on longer walks.
• Reliable waterproofing with breathable membrane keeps feet drier than non-waterproof options.
• Good traction on mixed surfaces thanks to the rugged rubber outsole and 4mm lugs.
• Durable leather construction that stands up to regular outdoor use when cared for properly.

Cons

• Some users find the sole stiff at first, which can feel hard on very long or technical hikes until broken in.
• A few reports indicate mixed longevity of the outsole; wear patterns vary with heavy use.

Specifications

Brand	KEEN
Upper material	Premium leather and breathable performance mesh
Waterproofing	KEEN.DRY waterproof breathable membrane
Outsole	KEEN.ALL-TERRAIN rubber with 4mm multidirectional lugs
Closure	Easy Speed Lace system
Support	Stability shank and removable footbed with arch support
Fit	KEEN Original Fit (roomy toe box)

Our Verdict

The KEEN Men's Headout Mid is a solid, versatile mid-height hiking boot that balances waterproof protection, breathable comfort and durable materials. It is a good value for hikers and outdoor workers who prioritize toe room and all-terrain traction; those seeking a very narrow fit or ultra-flexible sole should consider other options.

Frequently Asked Questions

Are these boots fully waterproof?
The KEEN.DRY membrane provides waterproof protection while allowing vapor to escape, so they perform well in rain and puddles but should be dried and cared for after heavy exposure.

Do they run true to size?
KEEN Original Fit tends to be roomier in the toe box; some customers find the length standard but the overall fit wider than narrow models, so try the usual size or size down if you prefer a snug fit.

Can I replace the insole?
Yes, the removable footbed allows you to swap in custom orthotics or new insoles for extended comfort and support.