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I grew up in the age of wannabe gangster rap. I’m not talking about the real gangster rap of the early- and mid-nineties; I’m talking about the faux-stuff of the early 2000s. If you were in high school or college then, you can probably still recite lyrics from Eminem, 50 Cent, or Nelly, even if—like me—you were never a fan. And if you’re a child of this era, you probably remember the footwear of choice for many rappers were the Timberland boots, dating back to the days of Tupac, Biggie, and the Wu-Tang Clan. It was this popularity in the hip-hop community that helped propel Timberland into the billion-dollar company it is today. I tell you all of this because as of a month ago, this was the extent of my knowledge about the brand. 

It’s about here where I feel I should confess that I’m a bit of a cheap-ass. This is why, when my editor asked me a month ago if I had a pair of hiking boots, I was a little embarrassed. Up until then, I was getting by on several pairs of old Army boots (I can feel your ridicule already) and a pair of Merrell boots that I purchased eleven years ago for an excursion through Torres del Paine National Park in the Patagonia region of Chile. To say these boots were battered would be an understatement, and when I started browsing brands to test, I was surprised to find Timberlands so highly rated in the hiking category. 

On Amazon, the highest-rated Timberland boots are the Timberland White Ledge Mid Waterproof hiking boots, which have over 36,000 ratings and still average 4.5 stars. On top of this, the Timberland White Ledges are moderately priced, starting at $89.95 on Amazon (price is dependent on size availability, as these boots are no longer carried on the Timberland website), which means you can likely pick up a pair for just under one Benjamin. Here’s why they may end as your next hiking boots of choice.


The boots arrived, as expected, in a standard-size shoe box. The box itself was olive green cardboard, with the trademark Timberland tree logo emblazoned on the top. It was apparent from the outset that Timberland is an environmentally conscious company, as a note on the back of the box indicates the box is made from 100 percent recycled material, to include water-based inks. The note also encourages the buyer to reuse the box and then ultimately recycle it again. I appreciated this, as I too enjoy environments and would like to help sustain the one we have with the hope that the planet will decide to stick around for a bit.

Timberland White Ledge Mid Waterproof Ankle Boots
Timberland White Ledge Mid Waterproof Ankle Boots (Brett Allen)

To drive this point home, the Timberland folks included a plastic wrap insert on which was printed a facts sheet, listing all the environmentally responsible aspects of the boots. This list includes the leather tannery ratings, percentage of recycled material used, renewable energy used in production, and even the amount of trees planted by the Timberland company from 2001 to 2017 (9.6 million trees). Now you might be thinking, “how ironic that they’d print all these environmental facts on a sheet of plastic wrap,” which we all know is a favorite food and choking hazard of adorable baby seals. I was thinking the same, until I realized the note on the plastic stating that the wrap itself was made from 100 percent recycled materials. It also encourages the reader to recycle all packaging material after use. Baby seal saved. Touché, Timberland. 

Timberland White Ledge Mid Waterproof Ankle Boots
Timberland White Ledge Mid Waterproof Ankle Boots (Brett Allen)

The first thing I noticed when I removed the boots from the box, was how soft the leather already felt. I’ve owned pairs of leather shoes and boots in the past and have always found them rigid upon initial purchase, but the Timberland White Ledges were pliable and soft right out of the box (except for the heel counter, which I’ll discuss later). The boots were much lighter than pairs I’ve previously owned (weighing in at 1.1lbs each), which was surprising for a mostly leather boot. This is a big positive, considering extra weight means extra exertion on the trails. The next thing I noticed was the thickness of the boot’s collar. The collar on the Timberland White Ledges measures at 1.25 inches thick, compared to a similar style ankle boot, the Nortiv 8, which had a collar thickness of .75 inches. The collar is meant to provide a good snug fit, while sealing the ankle off from pebbles, dirt, and debris from the trail and providing ample cushion to keep the boot from rubbing on the Achilles tendon. The leather upper and the collar are all cinched together by rustproof speed-lace hardware and two sets of lace hooks at the top. The outsoles of the Timberland White Ledge boots are standard rubber and the lug pattern is set fairly wide, which is good for shaking off mud and gravel and increasing traction on wet terrain. When I finally put the boots on, I was initially struck by how deep my heels sat in the boots. Even with my arch supports (I have flat feet and bad ankles—if I were a horse, they’d have shot me a long time ago), my heels seemed to sink abnormally deep, but the cushion of the collar gave me hope that there wouldn’t be excessive chafing.

How we tested the Timberland White Ledge Mid Waterproof hiking boots

Timberland White Ledge Mid Waterproof Ankle Boots
Timberland White Ledge Mid Waterproof Ankle Boots (Brett Allen)

Like with any pair of new shoes, it’s important to break in a new pair of hiking boots, and there are many schools of thought on how to effectively do this. Some people like to start slowly, wearing the boots around the house, doing light, everyday activities. Some people take the boots out for frequent but shorter hikes, and some people like to soak their boots in water and then wear them wet in order to better form the leather to their feet. Then there’s always the blister farmers. These are the suckers for punishment, the folks who take the boots straight from the box and hike in them for miles, until their socks are full of blood and their toes look like hamburger meat. This is not the preferred method. 

With the leather as soft as it already was, I didn’t think soaking the Timberlands was necessary and I decided to take them on some short hikes to get the feel for them. To do this, I took the boots out on the Dragon Trial, which is a series of hiking/biking trails around Hardy Dam Pond in mid-Michigan. I put the boots to a light test over moderate terrain, while periodically climbing down rooted, sandy banks to accompany my children to the water’s edge. The deep treads on the soles of the boots made climbing down steep embankments and over slippery roots quite easy. On the bank of the Hardy Dam Pond, I was able to test the boot’s waterproof claims and stood submerged up to the lower ankles for several minutes with my feet remaining bone-dry. Overall, we hiked a distance of a little over one mile, but I spent a total of about two hours wearing the boots that afternoon (pre-hike and post-hike doing light activity around the house and yard). The initial test was very positive and I was surprised at how comfortable the boots felt, despite the toe box being a little narrow for my wide feet. It should be noted that the Timberland White Ledge boots do come in wide sizes, but I often find that these wide cuts are often too wide for my feet and the excess room causes slipping and extra friction inside the boots.

Timberland White Ledge Mid Waterproof Ankle Boots
Timberland White Ledge Mid Waterproof Ankle Boots (Brett Allen)

The success of the initial test made me a little over-confident in both the boots and the toughness of my feet. Naturally, I decided to take the boots out on a longer hike with a little weight on my back. Pride cometh before a fall and this was a classic blister farmer blunder. With a 45-pound pack on my back and a head full of cocky confidence, I took off from my house on a humid, 90-degree afternoon. All was good until about the two-mile mark, when I started noticing the first twinges of a hotspot along my right Achilles tendon. Undaunted, I continued on, wanting to reach at least an hour of exertion before turning around. At the 30-minute mark, the pain was rising and a hot spot was developing on my left Achilles, too. Unfortunately, given the nature of the route I chose, there was no option but to turn around and cover the same distance back. By the time I got home, after covering a total distance of five miles, I had two quarter-size blisters in identical locations on each Achilles tendon. Not ideal. 

I was forced to wait several days for the blisters to heal before I could test the boots anymore. Before I tried them again, I added heel inserts under my orthotics to help lift my foot out of the heel cup and move the tender backs of my ankles into a more favorable position. I also took the extra time to soak the boots in warm water and then wore them wet for nearly a full day as they dried. The heel counter (the piece of leather making up the back of the boot) had been noticeably stiffer than the rest of the boot from the start, which I believe led to the excessive friction causing the unfortunate blisters. After soaking them, I’ve taken the boots on several hikes covering distances between five and seven miles and, with the added height of the heel inserts, I haven’t had additional issues with blisters or hot spots.

Timberland White Ledge Mid Waterproof Ankle Boots
Timberland White Ledge Mid Waterproof Ankle Boots
(Brett Allen)

What we liked about the Timberland White Ledge Mid Waterproof hiking boots

There are a lot of things to like about the build of the Timberland White Ledge Boots, namely the softness of the leather and the overall comfort of the fit. The boots seem to stand up well to the waterproof claims, having been pitted against wet grass, muddy roads, and even being partially submerged in a pond. Not once did my feet get wet from outside factors. A large part of this is due to the boots’ fully gusseted tongue, which keeps water out even when submerged over the laces.

The environmentally responsible practices of Timberland are another big plus for any nature lovers and, as noted before, the Timberland White Ledge boots come with a breakdown of some of the boots’ conscientious production features. The leather in the Timberland White Ledge boots is sourced from LWG silver-rated tanneries (LWG is the Leather Working Group and they evaluate the environmental compliance and performance of leather manufacturers). The list also indicates the boots are made of 67 percent recycled, organic, or renewable materials and that they are 97 percent PVC-free. Now I see why rappers love Timberland so much. Mother Nature is dope.

What we don’t like about the Timberland White Ledge Mid Waterproof hiking boots

The heel counter of the Timberland White Ledge boot seems to be almost too concave, creating additional contact between the interior surface and the Achilles heel. This, however, was quickly remedied by using inserts to adjust the height of my foot within the boot. After the initial blister issues, I checked the Amazon reviews to see if this was a common complaint, but I was unable to find any negative reviews about that particular problem. This leads me to believe I have freakishly structured ankles, which doesn’t do much for my self-esteem, but is an important piece of information to have for future boot purchases. 

The only other complaint I have about the Timberland White Ledge boots was the breathability. I understand that when you manufacture a boot to be waterproof, you tend to sacrifice opportunities for airflow in order to keep it water-tight. With anything, it is important to choose gear that makes sense for the environment you’re operating in, and perhaps wearing these boots in 90-degree weather is not optimal, as my feet often became overheated during hikes. Fortunately for me, Michigan offers a wide variety of weather opportunities and I look forward to putting these boots through additional testing in the fall and winter months ahead. 


The Timberland White Ledge boots are well-made and easy to break in. They live up to everything they’re advertised to be and are a decent, environmentally friendly option for any outdoorsman on a budget. However, if you plan to try them out, you may have to scoop them up soon while the supply lasts. After wearing these boots, I wouldn’t hesitate to look at other Timberland styles for my next hike or R&B album cover.

FAQs about the Timberland White Ledge Mid Waterproof hiking boots

Q. How much do the Timberland White Ledge Mid Waterproof hiking boots cost? 

A. Amazon has the starting price for these boots at $89.95, but prices vary on size and availability, as these boots no longer seem to be available directly from Timberland. They can also be found through DSW, REI, and other hiking boot retailers.

Q. How was the sizing of the Timberland White Ledge Mid Waterproof hiking boots? 

A. The recommendation from the Amazon page was to purchase the boots true to your normal shoe size. I regularly wear a men’s size 11.5 running shoe, so that was the size boot I ordered and the length was just about perfect. As I stated before, the toe box seemed to run a little narrow, but not enough for me to jump to the wide cut.

Q. Will wearing Timberland Men’s White Ledge Mid Waterproof Ankle Boots make me a better rapper? 

A. Unlikely. The Timberland boots popular with many hip-hop artists was a completely different style of boot. If you’re looking to improve your flow, I’d recommend the Timberland 6” Work Boots.

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Brett Allen is a humor writer and former U.S. Army Cavalry Officer who served from 2006 to 2010, largely with the 3rd Squadron, 71st Cavalry Regiment of the 10th Mountain Division. The events of his 2009 deployment to the Logar Province of Afghanistan became the inspiration for his recently published debut novel, Kilroy Was Here, which is a dark comedy highlighting the absurdities of war. Brett resides in Ada, Michigan with his wife and kids and is currently working on his next novel. He enjoys all things outdoors to include backwoods camping, backwoods cooking, hiking, and boating, but can more regularly be found mowing, weed whacking, or performing some other form of backbreaking yardwork.