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Last updated: 18 Feb 2020

15 Best Timberland Boots For Men (Review) in 2021

Timberland Men's White Ledge Mid Waterproof Ankle Boot

Timberland Men's White Ledge Mid Waterproof Ankle Boot

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Timberland Men's Davis Square Plain Toe Chukka

Timberland Men's Davis Square Plain Toe Chukka Boots

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Timberland Men's Killington L/F Chukka Walking Shoe

Timberland Men's Killington L/F Chukka Walking Shoe

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Show contents
By Instash
Published 08:10 am
Contents
  • The Best Timberland Boot For Men
  • 1 White Ledge Mid Waterproof Timberland Boots For Men
  • 2 Contrast Color Basic Timberland Boots For Men
  • 3 Larchmont Brown Chelsea Timberland Boots For Men
  • 4 Timberland PRO Men’s Pitboss 6 Boot
  • 5 Timberland GT Rally Mid Leather/Fabric Men’s Boot
  • 6 Timberland PRO Men’s Wedge Sole 6 Boot
  • 7 Timberland Men’s World Hiker Mid Ankle Boot
  • 8 Timberland PRO Men’s Disruptor Oxford Alloy Safety-Toe EH Work Shoe
  • 9 Timberland Men’s Chocorua Trail Mid Waterproof
  • 10 Timberland Men’s Killington L/F Chukka Walking Shoe
  • 11 Timberland Men’s Earthkeepers Rugged Boot
  • 12 Timberland Men’s Davis Square Plain Toe Chukka
  • 13 Timberland Men’s Logan Bay Boot
  • 14 Timberland PRO Men’s Powertrain Industrial & Construction Shoe
  • 15 Timberland PRO Men’s Titan 6

If you are after only the best and high-quality Timberland boots for men, you are in the right place. No doubt, Timberland Boots are one accessory that can be found in the shoe closet of many a manly man. The iconic Timberland boots have been considered an absolute classic for over 40 years. Not only are they comfortable when worn, but they also offer the wearer a very well polished urban swag.

Although this eclectic blend of urban and preppy is what makes the American legend, Timberland so popular, its humble beginnings started from a small village in Newmarket, New Hampshire. In 1973, Sidney Swartz designed his first worker’s shoe, the world-famous Timberland 6-inch boot was one of the first waterproof leather boots. The shoes have quickly consolidated in the market and are still very popular today, with the same sturdy quality as when they were first created. If you are after a pair, start by reading our list below of the best Timberland boots for men.

The Best Timberland Boot For Men

1
White Ledge Mid Waterproof Timberland Boots For Men

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timberland men's white ledge mid waterproof ankle boot
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When it comes to camping in the great outdoors, in a man versus nature type situation, you need the right footwear for the job. The Timberland Men’s White Ledge Mid Waterproof Ankle Boot is a top choice in Timberland hiking boots. Made of 100% pure waterproof leather, some light drizzling or a little mist is no cause for alarm. You can continue exploring those trails while enjoying the feel of raindrops through your shirt without worry of moisture getting the better of your feet.

Its rubber sole is strategically curved in the pressure point of your foot to support the braking, accelerating and climbing motions your feet need for better traction out on the trail. Even on the most uneven terrain, its padded collar protects your ankle from the biting into flesh, which is very common with boots that have no such padding. These features make movement in these Timberland boots so much more comfortable for use over extended periods. No doubt, out on the trail is no place to start battling with ill-fitting shoes.

Key Features:

Rubber soles for improved traction

Made with 100% waterproof leather

Padded collar and tongue to give ankle comfort

Comes with moisture wicking removable footbed

Specification:
  • BrandTimberland
  • Weight12 ounces

2
Contrast Color Basic Timberland Boots For Men

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timberland men's 6
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If you are a builder working hard out there pitted against the elements, constructing roads, bridges and any other architectural wonder for the rest of us, your feet needs the right Timberland pro work boots for the occasion. The Timberland Men’s 6″ Basic Contrast Collar Boot is a good choice for working out in the snow or rain. Its waterproof leather keeps your feet warm and safe from moisture inducing fungus and the synthetic rubber lug outsoles protect you from involuntary falls that will only land your face first on the ground.

The rubber soles also keep your feet firmly planted on the ground with a good, non-sliding grip. It’s stylish two colour design offers a light tan leather that makes up the larger part of the boots and a dark brown band around the ankle that is very pleasing to the eye. Comfort, protection and sophistication all in one Timberland footwear. What is not to love about it?

Key Features:

Available in black, wheat and rust nubuck colors

Waterproof for use in rainy or snowy weather

Synthetic sole is anti-slip with a good grip on the ground

Stylish two color design

Specification:
  • BrandTimberland
  • Model6
  • Weight2 pounds

3
Larchmont Brown Chelsea Timberland Boots For Men

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This easy to slip on ankle boot with its breathable and moisture wicking mesh lining is by far one of the best Timberland boots out there in the market. The Timberland Men’s Larchmont Brown Chelsea Boot is one perfect for all occasions. Stylish and elegant, they work as well for a picnic in the park as well as a quick shopping trip with wifey; yes they are that comfortable. Even better, they pair well with some denim and a sporty tee shirt, as well as a dress shirt on some chinos.

With a 5.0 out of 5-star rating by 100% of users, this is definitely one time it pays to join the Joneses. This top-notch shoe brand is obviously on to something here. These casual boots are comfortable right out of the box (this means no breaking in time required). Users who have had theirs for over three years swear by it, and as it is an ankle boot, it fits snugly under your trouser with no struggles to tie up loose laces.

Key Features:

Ankle boot with no laces

Casual boot suitable for all occasions

Comes with a padded and removable insole

Fitted with moisture-wicking mesh lining

Specification:
  • BrandTimberland
  • ModelA13HZ-M

4
Timberland PRO Men’s Pitboss 6 Boot

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timberland pro men's pitboss 6
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The ‘Pitboss’ soft toe boot is one Timberland pro work boot that should be in every outdoorsy man’s shoe closet. Smart looking and durable, the Timberland PRO Men’s Pitboss 6″ Soft-Toe Boot firmly meet the American National Standards Institute’s (ANSI) approved safety standards. Working in an environment with a lot of oil spills and other slippery materials? Then they are the right boots for you as these babies are anti-slip thanks to its oil resistant outsoles.

Working in such high-performance conditions often require being on your feet for hours on end. These pro work boots do not sacrifice comfort for stamina. Its PRO 24/7 Comfort Suspension technology is built into the sole to support the foot arch making it comfortable for prolonged standing without causing back pain or any other structural issue. You are safe from toe pain after foot swelling from hours of standing with its roomy toe section. The removable insole is an added comfort feature that protects your feet from blistering.

Key Features:

Oil resistant

Made with comfort suspension technology to prevent foot fatigue

Available in brown and wheat colours

Rubber sole protects wearer from slipping or possible electric shocks

Specification:
  • BrandTimberland
  • ModelTB033046214
  • Weight3 pounds

5
Timberland GT Rally Mid Leather/Fabric Men’s Boot

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timberland gt rally mid leather/fabric men's boot
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This sporty looking, Timberland hiking boot is like having the comfort and compact look of a sneaker and the durability Timberland boots are known for all rolled up in one. Made of part leather and part mesh, the Timberland GT Rally Mid Leather/Fabric Men’s Boots are perfect for hitting the hiking trail. With its SensorFlex technology, your under feet enjoy all the support possible in any kind of terrain you could possibly encounter.

With its vintage look, your feet will be the cynosure of all eyes. Talk about positive feedback. Its casual look makes it great for use in a number of situations. Even when not out on the trail, you can totally rock these Timberland field boots for a quick walk around the block to clear your head. They are that comfy. Available in seven other attractive leather – mesh colour combinations, you can always find one to match any outfit or occasion.

Key Features:

Available in seven colour options

Classy leather – mesh pattern

Work boot with a sneaker-like look to it

Rust-resistant lace hardware

Specification:
  • BrandTimberland
  • ModelTB0A1QD1C64
  • Weight3 pounds

6
Timberland PRO Men’s Wedge Sole 6 Boot

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timberland pro men's wedge sole 6
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These next rust coloured pure leather Timberland pro boots are a favourite among men who work with iron on rough surfaces, where one needs a firm grip on the ground. The flat rubber soles of the Timberland PRO Men’s Wedge Sole 6″ Boots sure sees to that. This ankle lace up boot has a moccasin style stitching on the front toe section of it. When you have your work denim pulled over the ankle part, you could literally have folks thinking you have a nice and comfy pair of moccasins on.

Its white rubber sole provides an attractive contrast to the rust coloured leather of the boot that would look great paired with some dark denim jeans on an autumn day. With its inbuilt anti-fatigue technology, you can work all day and then some without falling victim of foot or back pain. Available in size 7 medium all the way up to size 15 wide, any man with an eye for style can easily get his feet in one of these Timberland leather boots.

Key Features:

Available only in rust colour

Contemporary white rubber sole contrasts against rust coloured leather

Front toe box has moccasin style stitching

Fitted with anti-fatigue technology

Specification:
  • BrandTimberland
  • Model53009
  • Weight4 pounds

7
Timberland Men’s World Hiker Mid Ankle Boot

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timberland men's world hiker mid ankle boot
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Are you the kind of man who prefers snug yet sturdy shoes on his feet when out and about? Do you like the comfort of having durable shoes that are ready for any eventuality but still classy enough that you don’t look awkward at your neighbour’s barbeque? If yes, then the Timberland Men’s World Hiker Mid Ankle Boot is the right Timberland suede shoe for you. With a 4.3 out of 5-star rating by 73% of Users, these Timberland suede boots come with an EVA footbed that provides unparalleled comfort to users.

Ethyl Vinyl Acetate (EVA) is a foot saving material that gives stability to the foot. It is a soft, foamy material used in shoe production that is designed to support the wearer’s weight even under extreme conditions. Knowing that this is one of the best Timberland hiking shoes that are fitted with such high level-foot protection, you can jump, run and hike over any kind of terrain without fear of hard foot impact against the ground.

Key Features:

Ankle boot fitted with EVA protective footbed

Made of pure suede

Available in ten colours

Lightweight and comfortable

Specification:
  • BrandTimberland
  • ModelA1QFL
  • Weight1.09 pounds

8
Timberland PRO Men’s Disruptor Oxford Alloy Safety-Toe EH Work Shoe

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timberland pro men's disruptor oxford alloy safety-toe eh work shoe
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These next Timberland shoes for men are high-quality footwear made of 100% canvas. Low slung with heat resistant, rubber soles and alloy safety toes, the Timberland PRO Men’s Disruptor Oxford Alloy Safety-Toe EH Work Shoe is one of the best in foot protective, safety wear. Made with black canvas, these shoes have two variations with one having white soles and toe section while the other is pure black, through and through.

After a long, hard day at work and you just can’t wait to get your feet out in the open air, tugging off a pair of boots, laces and all can get to be quite exhausting. With this canvas shoe though, slipping it on and off is a breeze. The steel toes give your delicate toes added protection from bruising especially if you do welding in your line of work. Having sparks land on your toes will have you screaming like a banshee in pain without the protection from the toe caps.

Key Features:

Made of pure canvas

Available in black or white soles and toe caps

Easy to slip on and off

Can be purchased for as low as $28.00

Specification:
  • BrandTimberland
  • ModelDisruptor Oxford Alloy Safety Toe EH-M
  • Weight1.5 pounds

9
Timberland Men’s Chocorua Trail Mid Waterproof

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Finally made up your mind to tick trekking the great Amazon forest off your bucket list? Well, before you head out into the dense, moist vegetation, make you have the right footwear for the job. The Timberland Chocorua Trail mid Waterproof is one Timberland waterproof boot that was made for times like this. Designed with 100% pure, waterproof leather with EVA midsoles for flexibility and ground impact absorption, these boots are comfort and durability all wrapped up in one stylishly rugged package.

Its stylishly rugged look makes it perfect for when you are off the trail too. Pull on the boots for a night on the town. These boots are so sturdy that even one user has commented, “they are so tough, if a tiger tried to eat you, you could shove your boot in its mouth and when he bit down all his teeth would break off!’. Now you can strut around that East side of town without fear, being sure that a swift kick to the nuts with these boots would have any would-be assailant doubled over.

Key Features:

Waterproof

Sturdy with rust-proof hardware

Designed with mesh uppers

Anti-fatigue technology

Specification:
  • BrandTimberland
  • Weight2 pounds

10
Timberland Men’s Killington L/F Chukka Walking Shoe

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timberland men's killington l/f chukka walking shoe
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The Timberland Men’s Killington L/F Chukka Walking Shoe is one artistic number which features a mix of well-placed mesh and that signature dark tan leather Timberland is known for; no doubt, this is one of the most comfortable Timberland shoes. Walking the street, running errands or even just hanging out in the park is fair game with these shoes. They are very comfortable and lightweight with breathable mesh so your buds don’t scurry for the hills when they see you reaching down to take it off. The Ortholite footbed has seen to that.

Dark, grey, olive, whichever shade you prefer, these shoes are available in that colour. You could go with the navy full grain option that would work with just about any outfit or you can decide not to play so safe and try the cool grey which would make a bold statement. What a fashionable way to draw attention to your feet!

Key Features:

Designed with breathable Ortholite Footbed

Sensor flex technology gives underfoot support

Can be found in six different colour selections

Can be used both on and off the hiking trail

Specification:
  • BrandTimberland
  • Weight12 ounces

11
Timberland Men’s Earthkeepers Rugged Boot

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timberland men's earthkeepers rugged boot
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Want to save the earth and look good while at it? Then hook yourself up with one of these red-brown Timberland leather boots. The Timberland Men’s Earthkeepers Rugged Boot has its lining made with recycled polyethylene terephthalate (PET). This is a tree huggers dream come true. You get to do your quota in environment protection without compromising style. With its rubber outsoles giving you anti-slip protection and lots of traction, you can finally help Grandpa do some work on the ranch. No more fear of sliding and falling face first into horse dung.

Designed with the ‘high-performance male spending days on end on their feet’ in mind, the anti-fatigue technology built into the midsole gives comfort. This environment-friendly footwear even has laces made from organic cotton with no chemicals used at all in production. Going green has never looked so good.

Key Features:

Environment-friendly

Made with organic and recycled material

Available only in red-brown colour

Made of pure leather

Specification:
  • BrandTimberland
  • ModelEarthkeepers Rugged
  • Weight5 pounds

12
Timberland Men’s Davis Square Plain Toe Chukka

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timberland men's davis square plain toe chukka
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These next Timberland shoes for men are great shoes that look pretty much like some kind of cross between the Timberland Men’s 6″ Basic Contrast Collar Boot and the Timberland PRO Men’s Disruptor Safety-Toe Work Shoe. Now, with the Timberland Men’s Davis Square Plain Toe Chukka you can enjoy having that signature Timberland boots wheat nubuck colour with the dark brown collar contrast on an ankle shoe with a bit of tan canvas and leather going on. Just like a boot but in a chukka boot form.

Available in bold burgundy and dark ruby nubuck, you sure can make a style statement with this Timberland footwear. With light coloured shoes, the fear of getting tough stains that mar their beauty is ever present. Timberland has thought of that though and factored in Defender Repellent Systems treatment that are water and stains resistant. What a relief! Now you can relax when your cute baby daughter decides to get her grubby, applesauce covered hands all over your shoes.

Key Features:

Can be found in bright colours such as burgundy

Designed with water and stain repellent technology

Comes with a padded collar

Lining is fitted with breathable mesh

Specification:
  • BrandTimberland
  • ModelA10HG
  • Weight5 pounds

13
Timberland Men’s Logan Bay Boot

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No matter the type of man you are, from the urban guy who likes a little limp in his swag, to the classic country lad, every man appreciates the Timberland brand for its modern style and comfortable wearability. Even with the Timberland Men’s Logan Bay Boot on your feet, with its trendy antique vintage look, you are still offered a very modern appeal as a modern man. The ability to consolidate the old with the new is what makes Timberland very unique as a brand.

This airy versatile shoe is perfect for all seasons, come rain or shine, whilst being a great robust and water-resistant specimen. There are simply no limits. The aim of Timberland is to always produce durable, fashionable shoes that make you completely satisfied. And Men’s Logan Bay Boots cuts it by far.

Key Features:

Premium leather uppers

Anti-fatigue removable footbed

Arch support

Gripstick rubber

Specification:
  • BrandTimberland
  • ModelA1R1U
  • Weight3.76 pounds

14
Timberland PRO Men’s Powertrain Industrial & Construction Shoe

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timberland pro men's powertrain industrial & construction shoe
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Construction workers!? Where y’all at? There is great news. Timberland has got your feet covered with this alloy toed construction shoe. Civil engineers and every other fellow working on rough terrain and exposed to harsh chemicals, you sure need the protection these Timberland shoes can provide. Made of 100% ripstop nylon with a synthetic sole that offers increased grip and traction, you can walk over that granite without slipping in the Timberland PRO Men’s Powertrain Sport Alloy-Toe EH Industrial & Construction Shoe. Even better, should you find yourself in a wet yet electrically charged environment, this Timberland footwear would literally save you from getting electric shocks.

With the contemporary design with bright electric blue or orange woven into the ripstop nylon, these athletic looking work shoes will make you look super fly. You can finally part ways with drab-looking work accessories with these shoes. The alloy toe caps give added foot protection. Flexible and comfortable straight out of the box, no breaking in period is required.

Key Features:

Synthetic sole gives great grip and increased traction

Athletic, multi-colour design

Comes with electric hazard protection

Available in three colours

Specification:
  • BrandTimberland
  • ModelPowertrain Sport Alloy Toe EH-M
  • Weight2 pounds

15
Timberland PRO Men’s Titan 6

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timberland pro men's titan 6
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These next sturdy Timberland leather boots with its dark brown colour and synthetic soles exude pure, undiluted masculinity. Made with rich, chocolatey brown leather with a coffee brown collar, the Timberland PRO Men’s Titan 6″ Safety-Toe Boot are very easy on the eyes. You can totally rock them to the pub or for that get together on the ranch.

Lots of shoes look the part but can’t do the work they were designed for; however, that is not the case with these boots. Worried about all that leather trapping heat and moisture on your feet? You can breathe easy, as these Timberland boots offer a moisture-wicking lining treated with Agion, an antimicrobial technology used in preventing the growth of microbes. With its Titan safety toe cap and electrical hazard protection meeting international safety standards with ease, you can totally trust Timberland to take care of your feet.

Key Features:

Available in four colours

Fitted with Agion treated lining

Moisture-wicking lining

Can be used both for work or casually

Specification:
  • BrandTimberland
  • ModelTB026063214
  • Weight2 pounds

Timberland Boot For Men Buyer’s Guide

Features To Look For In Timberland Boots

Material - Timberland is a very eco-friendly brand keen on environment conservation. All leather products used in making the boots are sourced from dairy farmers where animals are raised for food and processed according to USDA standards. In fact, Timberland has banned the sourcing of animal hide from countries known to violate animal husbandry guidelines.

Only 100% recycled PET is used in making the lining and the upper part of the shoes are made of 100% recycled canvas. Timberland does not use materials derived from any animal that was killed purely for the use of their hides. Animal lovers can relax, no fur is used in any Timberland product.

Toes Protection - Timberland is big on toe protection for wearers working in hazardous and demanding environments. The Timberland pro work boots are fitted with lightweight steel alloy for field professionals who are keen on all the toe protection and comfort their footwear can provide. Most Timberland boots are designed with either alloy or steel toe boxes that are covered with epoxy to prevent corrosion when in contact with harsh chemicals.

Timberland boots meet all US and internationally approved impact and compression safety laws. These Timberland boots toe boxes are very roomy thus protecting your feet from the numerous hazards of the work environment.

timberland boots

Weight - The weight of Timberland boots and shoes differ based on material they are made of. Generally, the leather boots weigh a lot more than the canvas type and those that are fitted with steel-toe boxes are possibly the heaviest, while shoes made with canvas or nylon are the lightest.

A pair of 6” inch boots would weigh in at about 4.5 pounds while most steel toed boots would weigh about 5 pounds. The kind of soles used also plays a big role in shoe or boot weight. A rubber sole is often heavier than a synthetic one. Rubber soles though have the ability to give better grip and traction.

Fit - Timberland has a boot or shoe for every man in any kind of occasion. Designed with foot protection in dangerous work conditions in mind, these boots are so stylish they are seen countless times on the runway and are designed for classy men making bold fashion statements. They can be worn in any season on denim jeans, chinos, overalls or even shorts for the very bold man. Whichever way you choose to rock those ‘Tims’, just make sure your pants hem remains behind the boot’s tongue. Sizing is a thing when selecting the Timberland boots right for you. When choosing some ‘Tims’, make sure to pick a size down from your regular shoe size.

Comfort - Timberland shoes are designed with all kinds of gear to ensure maximum comfort for the wearer. Whether you are hiking, walking or have to spend long periods standing, you can be sure Timberland does not compromise comfort. Its SensorFlex technology which took about three years to develop provides cushioning and optimal flexibility to your underfoot allowing you to be on your feet for hours without pain.

Its padded collar protects your ankles while the breathable, moisture-wicking mesh lining keeps your feet free from moisture and odour free. In subzero temperatures, they keep your feet nice and warm. EVA midsoles do their bit in adding a spring to your step.

timberland boots

Waterproofing - With an array of Timberland waterproof boots to choose from, a rainy day doesn’t limit you to wearing Wellingtons. You can still pull off the “I just stepped off the GQ magazine cover” look with your feet remaining nice and dry safely encased in waterproof boots. Even snow has nothing on you with Timberland waterproof boots. As the leather has silicone injected into it, your shoe could pick up a stain but no water or wetness whatsoever else will gain access to your feet. Even the seams are sealed with silicone so no water can get in through the stitching.

Durability - Timberland footwears are not one of those boots that need replacing every other month. Designed with rust proof material and waterproof leather, these well-built boots have superior protection from the elements and do not deteriorate easily. Its soles made of 100% recycled rubber not only provide enhanced traction and better grip but also reduce wear and distribute it evenly.

Rubber soles can last for over three years of active use and even more if used for more fashionable purposes, as they are not often affected by extreme weather. Loaded with 400 grams of downy fleece, in cold weather, your feet get all the thermal insulation they need.

timberland boots

Timberland: About the Brand

Timberland’s rich history in boot making dates all the way back to 1952 when it was known as the Abington Shoe Company. Thousands of silicone injected waterproof boots later, the company which came to be known as Timberland in 1970 had positioned itself strategically as a trusted shoemaker popularly known with its signature yellow boot. With the passing of each year, Timberland has worked with several other brands to come up boat shoes, suede boots, Chuck’s and canvas boots all to ensure every man, woman and child has a Timberland that speaks to the souls. With an over six decade history in boot and shoe making, you can walk tall with a pair of ‘Tims’ on your feet.

Timberland Boots FAQs

Q: What Materials Are Timberland Boots Made Of?

A: Timberland boots are mostly constructed with high-quality, full-grain nubuck suede leather, canvas, mesh lining, and ripstop nylon. Their seams are carefully sealed and allow for efficient water resistance whilst the thick sole made of rubber ensures optimal slip resistance and a long service life. All materials used are eco–friendly, recycled and do not involve the use of animals killed solely for their hides.

Q: What Socks Should I Wear With My Timberlands?

A: What best to wear with Timberland footwear if not Timberland socks? It’s not like you are backed into a corner with no choice, though, as Timberland offers an exciting plethora of socks. Prefer them with stripes, dots or plain? Timberland has got it. Ankle, shoe liner and even cooling socks to keep your feet dry; socks are all available for the picking.

timberland boots

Q: Should I Waterproof My Timberland Boots?

A: The Timberland boots of the waterproof variety do not require any additional waterproofing. Should you be exposed to wet or rainy conditions and you own suede, canvas or ripstop nylon made boots or shoes, you may choose to protect them with waterproof spray. Simply clean them of all dirt, remove the laces and give an even coat of waterproof spray all over it.

Q: How To Care For Timberland Boots?

A: For leather boots, applying the Waximum Waxed Leather Protector will keep them soft and oiled protecting the leather. Just make sure not to use this on nubuck or suede shoes. For those using the Suede Restorer Brush it will keep your boots looking sharp, giving them a whole new lease on life. For the canvas variety, help them last by keeping them dry.

For added protection, use the Balm Proofer XL All Purpose Protector immediately after purchase and every other week from then on. One measure that protects all ‘Tims’ no matter the material is to simply give it a break. Can’t wait to rock em again? Squeeze some newspaper into the boots to draw out the moisture and top it off with a healthy burst of some  Shoe Refresher to keep it smelling fresh.

Sources:

  1. Polyethylene terephthalate - Wikipedia
  2. Antimicrobial - Wikipedia
  3. Nubuck - Wikipedia
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