Taking on the challenges of the great outdoors requires being fully equipped with durable, dependable gear. When it comes to climbing trails and scaling peaks, you want every step to feel solid and secure, and you want your feet to stay warm and dry, which are exactly what you can expect from Timberland boots.
Timberland has been producing some of the toughest boots around for decades, and their lineup for mountain climbers and outdoor enthusiasts are as varied as ever. Still, there are a few that represent the summit of the brand’s efforts, which you’ll find in the list below.
Here are the best Timberland pro hiking boots under $100:
Comparison Chart
Timberland Men’s White Ledge
Key Features
- Made from premium 100% leather using seam-sealed construction
- Rust-proof lace hardware for speed and security
- EVA footbed and midsole absorbs every step and keeps feet warm
It should only make sense to start with the most highly reviewed and best-selling pair that Timberland currently offers, the Men’s White Ledge hiking boots. It’s a mid-cut seam-sealed waterproof boot with a solid rubber outsole designed to keep your feet warm and dry even in winter.
These brown and black Timberland hiking boots are very comfortable to wear, thanks to its EVA midsole and footbed absorbing the impact of every step. Its speed lace hardware stays secure with additional hooks on top and its tongue is fully gusseted. You’ll ascend tough trails confidently in these boots, and it looks good for everyday wear to boot.
Timberland Men’s Chocorua Trail
Key Features
- Fully waterproof construction with mesh uppers
- Timberdry membrane keeps moisture out
- EVA foam midsole absorbs impact
- Has a removable anti-fatigue footbed
Built using Gore-Tex boot technology, the Men’s Chocorua Trail is both durable and waterproof, while letting your feet breathe. It features Timberdry membranes, which are made from sustainable materials, that help your feet stay dry.
Trekking along rough terrain won’t strain your feet while wearing these green and brown Timberland hiking boots since its foam midsole is a compressed EVA layer. You’ll be able to go longer and farther on its anti-fatigue footbed, and its all-around solid construction will let you wear your Chocorua Trail for years to come.
Timberland Men’s Flume
Key Features
- Full-grain leather uppers and fully gusseted tongue
- Seam-sealed build provides firm waterproofing
- Lightweight cushioning from molded EVA sole
Made from premium 100% leather, these imported Timberland pro hiking boots are named after the lovely Flume Gorge in New Hampshire. It’s designed to provide maximum protection and comfort while you’re clambering up rocky ground.
With a compressed EVA footbed and midsole providing shock absorption and cushioning, the Men’s Flume feels thoroughly lightweight and mobile. Its seam-sealed construction will ensure dry feet and you’ll get lots of traction from the multidirectional lugs under its rubber outsole. Go from the trailhead to summit with your feet well-protected by these hiking boots.
Timberland Men’s Mt. Maddsen
Key Features
- Made from premium leather rated silver by the Leather Working Group
- Water-impermeable with TimberDry membranes
- Features lugs designed under the BSFP Motion Efficiency System
- Has an internal shank for added rigidity
Enjoy all-day all-terrain comfort with the Men’s Mt. Maddsen enveloping your feet. These black Timberland hiking boots feature the brand’s Anti-Fatigue technology meant for people who go long hours on their feet. Each step is supported by geometric cones molded into the midsole to return energy and minimize the impact. Along with specially aligned lugs placed in the right places, each braking, supporting, flexing, and propelling motion you take becomes more efficient.
The Mt. Maddsen is fully waterproof, made from authentic leather that’s been rated silver by the LWG. Expect extended performance from these boots, especially with the internal TPU shank adding torsional rigidity to its structure. If you need a pair of robust leather boots that can endure prolonged outdoor adventures, Timberland’s Mt. Maddsen will not disappoint.
Timberland Men’s Euro Hiker
Key Features
- Leather uppers are sourced from an LWG-accredited tannery
- D-ring rust-proof lace hardware with recycled laces
- Padded tongue and collar along with EVA midsole adds extra comfort
If backpacking and hiking across Europe sound like your idea of fun, you’ll love the combination of comfort and ruggedness in the Men’s Euro Hiker. These brown Timberland hiking boots are specially engineered to help you traverse extreme outdoor environments with superior support and protection.
The full-grain, silver-rated premium leather used for these Timberland pro hiking boots feature natural color and texture variations that make each pair unique. It fits comfortably thanks to a well-cushioned midsole and padded collar around the ankles. Whether you’re out in the mountains or out in the city, the Men’s Euro Hiker boots will make sure you feel confident.
Timberland Men’s Rangeley
Key Features
- 100% premium-grade leather and high-traction rubber sole
- Internal thermoplastic shank adds durability and abrasion resistance
- Adjustable lacing hardware and padded top for extra comfort
Ranging overland under diverse weather conditions won’t seem too bad if you’ve got a pair of these brown Timberland hiking boots on. The Men’s Rangeley offers a nice balance of protection and comfort to keep you gracefully lopping along natural trails or urban pavements.
You’ll get plenty of traction from the solid rubber sole underneath as well as plenty of arch support from its internal shank made from thermoplastic urethane. The midsole is molded to give your feet additional cushioning, making each step feel light and easy. Don’t be surprised if these imported Timberland boots are all you want to wear after you break them in.
Why Timberland boots are great for hiking and trekking
Timberland has been innovating outdoor footwear ever since the company’s inception, and their continued success only indicates the level of trust they’ve built with their happy customers. With these waterproof leather hiking boots on, you’ll be sure to get the best protection for your feet no matter where they take you.