10 Best Leather Walking Boots 2025 in the United States

The Timberland Men's White Ledge Mid Waterproof Hiking Boot in Black (size 9.5) is crafted from premium waterproof leather, making it a good choice for wet conditions. The fully gusseted tongue keeps debris out, while the rustproof speed lace hardware ensures durability in various weather conditions.

The ReBOTL fabric lining, made from recycled materials, adds an eco-friendly touch. The EVA footbed and midsole provide decent cushioning, enhancing comfort for long walks. Additionally, the rubber sole delivers good traction on different terrains, contributing to stability and support.

However, some users might find these boots a bit heavy compared to lighter alternatives, which could affect comfort during prolonged use. The breathability might also be less than optimal due to the full leather construction, potentially causing feet to get warm, especially in hotter climates. Despite these minor drawbacks, these boots offer solid performance for those seeking durable, waterproof walking boots with reliable support and traction.

The Timberland Mt. Maddsen Chukka Boot is made with premium full-grain leather, which means it's durable and should hold up well over time. It features TimberDry waterproof technology, so your feet will stay dry even in wet conditions, making it a good choice for walking in rain or damp environments. The fully gusseted tongue keeps out dirt and debris, which adds to comfort during long walks. Thanks to Timberland’s Anti-fatigue footbed, these boots offer good cushioning, reducing tiredness after a full day of wear. The rubber lug outsole provides solid traction and stability on various surfaces, helping to prevent slips. At around 3 pounds, they strike a decent balance, not too heavy but still supportive.

Because the boots use full-grain leather, breathability might be limited compared to boots with mesh panels, so your feet could feel warmer during hot weather. The ankle-height design provides moderate support, which is suitable for casual hikes or everyday walking but may not be enough for very rugged terrain or heavy backpacking. These boots are ideal for those wanting a stylish, waterproof, and comfortable leather boot for everyday use or light hiking rather than specialized hiking boots designed for extreme conditions.

The KEEN Men's Targhee 2 Mid Height Waterproof Hiking Boots are a solid choice for those needing reliable footwear for walking and hiking. Made from durable premium leather and breathable performance mesh, the boots balance toughness with comfort. The waterproof KEEN.DRY membrane effectively keeps feet dry, while the quick-dry lining is great for active use. They feature a high abrasion rubber toe guard for enhanced durability on rough terrains.

The external support shank and contoured heel add stability and ankle support, making them stable on uneven surfaces. The removable footbed with arch support provides good cushioning that resists compressing over time, adding to the comfort. Additionally, the 4mm multi-directional lugs and KEEN ALL-TERRAIN rubber outsole offer strong traction, especially in muddy or rocky environments, ensuring sure footing.

The boots are also thoughtfully designed with environmentally-friendly DWR to prevent the leather from drying out. However, they might feel a bit heavy at 1.12 pounds, which could be a drawback for some users looking for lightweight footwear. Breathability is decent but could be better for those who hike in very hot conditions. The fit is generally comfortable with ample space for toes to spread, but it’s essential to ensure the sizing is correct, especially for those with wider feet. This product suits hikers who prioritize durability and all-weather performance.