7 Best Timberland Hiking Boots in 2023
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Why trust us
Timberland is among the go-to brands when it comes to serious outdoor footwear. Their hiking boots are built to last and keep you going when the trail gets tougher.
We have tested 10+ incredible Timberland hikers to come up with our top picks. So whether you need the Swiss Army knife of kicks, a super-supportive Timberland boot, or something you can wear on dress-down Fridays, here is the place to be.
How we test hiking boots
We at RunRepeat always strive to create objective and easy-to-read reviews on the best Timberland hiking boots on the market. The details of our approach are as follows:
- To ensure that every review is free of bias, we buy Timberland hiking boots with our own funds.
- We test every Timberland pair in a variety of settings, including diverse terrain and wet conditions.
- To make our Timbs-centric reviews comprehensive, we take hundreds of opinions from professional testers and regular hikers and blend them with ours.
Having all that in the bag, we eke out a CoreScore. This RunRepeat-exclusive rating system helps us create this list of Timberland’s bests.
Best Timberland hiking boots overall
Timberland Euro Hiker
83
Good!
What makes it the best?
Euro Hiker's comfort is what dreams are made of. It's so much worth the investment especially when you take into account its weight, durability and grip. Recycled rubber is a nice touch! The Euro Hiker by Timberland may arguably be a cut above with its wealth of positive traits working into a fine synergy.
Pros
- Amazing in-shoe comfort
- Above-average traction
- Insanely lightweight
- Supportive arch
- Lasting construction
- Above-average traction
- Recycled rubber used
- Attractive design
- Affordable
Cons
- Subpar ventilation
- Unruly laces
Today's best price
Men
Women
Any color
Amazon
Free shipping
$85
Shoebacca
Free shipping & returns
$90
Shoe Mall
Free shipping
$91
Champs Sports
Free shipping & returns
$98
Finish Line
Free shipping & returns
$115
Stadium Goods
$139
Best Timberland waterproof hiking boots
Timberland White Ledge Mid Waterproof
88
Great!
What makes it the best?
This mid-top boot from Timberland has received a lot of praise from the outdoor community for its lightness, traction, and ankle support. On the other hand, its lack of success against water-related obstacles did not spark joy with several adventurers. All in all, the Timberland White Ledge Mid Waterproof has a generous set of pros that can go well with hiking trips that don’t have a lot of wet trails.
Pros
- Lightweight build
- No break-in period
- Grippy outsole
- Provides ankle support
Cons
- Ineffective waterproofing
- Insubstantial metal eyelets
Today's best price
Men
Women
Any color
Amazon
Prime & free shipping
$86
Zappos
Free shipping & returns
$90
Designer Shoe Warehouse
Free shipping
$110
Moosejaw
Free shipping
$120
Eastern Mountain Sports
$120
Best Timberland mid cut hiking boots
What makes it the best?
Timberland’s Mt. Maddsen Mid Waterproof earned the favor of the hiking community through its provision of superb comfort. Its versatility, and lightness were plusses to its already good reputation. However, it seems that it failed to satisfy some folks in terms of durability. With all that said, the Mt. Maddsen Mid Waterproof is a rewarding boot when it comes to trail performance; its durability remains a gamble, though.
Pros
- Comfy interior
- Commendable stylish design
- Versatile (outdoor and casual)
- Supportive arch zone
- Satisfying lightness
- Right-out-of-the-box comfort
- Effective waterproofing
Cons
- Not durable
- Too narrow
Today's best price
Men
Women
Any color
Zappos
Free shipping & returns
$84
Amazon
Prime & free shipping
$85
Shoebacca
Free shipping & returns
$100
Shoe Mall
Free shipping
$115
REI
Free shipping
$120
Stadium Goods
$179
Best casual Timberland hiking boots
Timberland Euro Trekker
86
Great!
What makes it the best?
Where mobility is of the essence, the Euro Trekker has the credentials to impress. Built around a low-profile last, this day hiking boot from Timberland offers precision and impressive tenacity on various terrain, whether level or mildly elevated. There's also its pub- or bar-worthy design and cheaper-than-most asking price to reel you in further.
Pros
- Exceptional comfort level
- Loosens up in no time
- Fantastic grip
- Lightweight
- True to size
- Dashing aesthetics
- Very affordable
- Cozy in chilly weather
Cons
- Not very protective
- Underwhelming arch support
- Tongue not gusseted anymore
Today's best price
Men
Women
Any color
Backcountry
Free shipping
$54
Shoebacca
Free shipping & returns
$90
Amazon
Prime & free shipping
$96
Zappos
Free shipping & returns
$101
Best Timberland day hiking boots
Timberland Chocorua Trail Mid Waterproof
88
Great!
What makes it the best?
A high-quality hiker that impresses many outdoorsy folks - this is the Chocorua Trail Mid. It's an all-around hiking shoe that is amazingly comfortable, supportive, and waterproof. Even more impressive is its lightness, which means you can use it for walking for long hours without feeling tired.
Pros
- Unbelievable comfort
- Excellent arch and ankle support
- Lightweight
- Wide toe box
- Waterproof
- Sturdy all-purpose boot
Cons
- Thin soles
- Lack of toe protection
Today's best price
Men
Women
Any color
Zappos
Free shipping & returns
$115
Amazon
Prime & free shipping
$115
Shoebacca
Free shipping & returns
$115
REI
Free shipping
$125
Moosejaw
Free shipping
$125
Eastern Mountain Sports
$125
Best value
Timberland Norwood Mid Waterproof
86
Great!
What makes it the best?
The Timberland Norwood Mid Waterproof was commended for its accurate fit and sizing. Despite these pleasing features, it was still not good enough. Its poor waterproofing, easily-scuffed upper, and unimpressive outsole were a letdown. Overall, before getting a pair of the Norwood Mid Waterproof from Timberland, one must evaluate her trail needs carefully.
Pros
- Runs true to size
- Lightweight
- Fits just right
- Adequate ankle support
- Versatile design
- Short to zero break-in period
Cons
- Insufficient waterproofing
- Thin threads
- Easy to scratch
- Lack of ventilation
Today's best price
Men
Women
Any color
Out of stock in all 50 shops
Timberland timberland hiking bootsMost popular Timberland hiking boots
Timberland World Hiker
83
Good!
What makes it the most popular?
With comments such as "a must-have" and "a dope shoe," the World Hiker from Timberland is a hype-worthy reintroduction of a '90s classic. A monster of a boot, this over-the-ankle hiker is amazing on trails and keeps you comfy and dry in wet conditions. And while it comes with no insulating tech, the experience you'll get from it is as if it has one.
Pros
- Lasts many years
- Waterproof
- Remarkable warmth
- Terrific workmanship
- Very protective
- Comfortable
- Definitely dapper
- Eco-friendly
Cons
- Heavy
- Not for wide feet
- Super pricey
Today's best price
Men
Women
Amazon
Free shipping
$140
Zappos
Running Warehouse
REI
Comparison of the 7 best Timberland hiking boots
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