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Shoes & Footwear > Men's Shoes & Boots > Men's Casual Boots & Shoes
Men's Casual Boots & Shoes Products from Timberland

Products
Timberland Amherst High Top Chukka Boot - Men's Timberland Amherst High Top Chukka Boot - Men's
Boots or shoes can be hard to decide between. Boots have their pluses, with extreme durability, and ability to withstand rough work conditions. Shoes on the other hand, are just more comfortable, and you've got the style points that a fresh pair of kicks with bright white soles add to any outfit. Boost you swagger with the Timberland Amherst High Top Chukka Boot, capturing the essence of a sneaker, with white outsoles and high tongues, and tough leather uppers and boot construction that means they will last. OrthoLite polyurethane footbeds provide all-day comfort, and SensorFlex system delivers support, independent suspension, and flexibility, so you'll be pumped to keep these on from slinging 2x4's at work in your Carhartts to throwing back a couple of pints of pale ale with your posse at the local watering hole.
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$124.95
Timberland Britton Hill Chukka Boot - Men's Timberland Britton Hill Chukka Boot - Men's
Polished without being too fancy, the Timberland Men's Britton Hill Chukka Boot offers casual-yet-refined style that you can take anywhere. And unlike many casual boots that focus on style without paying much attention to comfort, Timberland made sure to equip the Britton Hill with all the features needed to keep you comfortable when you're on your feet all day, including supportive Anti-Fatigue technology and a shock-absorbing SensorFlex triple-layer suspension system.
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$149.95
Timberland Britton Hill Waterproof Boot - Men's Timberland Britton Hill Waterproof Boot - Men's
When you have Timberland's Britton Hill Waterproof Men's Boots in your collection, there's no need to suffer all day with wet feet, or worse, wear ugly shoes just to keep your feet dry. These leather and nubuck beauties will put the rest of your shoes to shame, and they have a waterproof and breathable membrane that lets you cruise through puddles when you're walking from the workshop to the whiskey bar. Timberland's SensorFlex midsole and Anti-Fatigue Technology make long days at the table saw easy on your feet, and the recycled mesh lining moves sweat away from your feet when you're working hard on a soggy day.
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$199.95
Sale Price: $149.96
Timberland Carter Notch Chelsea Boot - Men's Timberland Carter Notch Chelsea Boot - Men's
Spending time to tie your shoes is overrated, so instead, pull on the Timberland Men's Carter Notch Chelsea Boot and use that time to floss or wash some dishes instead. The premium full-grain leather upper is totally waterproof, so those afraid of a little rain and puddle-splash need not apply. The internal mesh lining helps your feet breathe and is made entirely of recycled plastic bottles, so by rocking the Carter, you're breathing new life into old material. Plus, the removable footbed features anti-fatigue technology that is an absolute blessing if you happen to work on your feet.
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$149.95
Timberland Carter Notch Waterproof Chukka Boot - Men's Timberland Carter Notch Waterproof Chukka Boot - Men's
If you're looking to dress to impress, but also want some utility out of your kicks, look no further than the Timberland Men's Carter Notch Waterproof Chukka Boot. Besides being fun to pronounce, the Chukka is a stylish waterproof shoe that's great for navigating dreary days on the way to or from work, a meeting, or a date. Let's be honest, the premium full-grain leather uppers look good, and the Timber-Fry waterproof membrane is crafted from 50% recycled plastic bottles, so with every step taken, you're keeping waste out of the landfill and using it to keep your feet warm, dry and cozy.
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$139.95
Timberland Coltin Mid Boot - Men's Timberland Coltin Mid Boot - Men's
Pairing supple leather uppers with a mid-top silhouette, the Timberland Men's Coltin Mid Boot brings rich detail and streamlined sophistication to urban environments. This mid-top boot features an unlined leather upper with a protective coating that repels oncoming showers, puddle splashes, and stains from setting in. The SensorFlex Comfort System is a triple-layered suspension system that absorbs jarring vibration, while remaining light and limber underfoot. Rubberized lugs maintain traction for treading across city scapes and slippery surfaces.
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$134.95
Sale Price: $101.21
Timberland Eagle Bay Leather Boot - Men's Timberland Eagle Bay Leather Boot - Men's
Do you love Timbs, but can't justify walking around in a heavy soled boot all day long' Check out the Timberland Eagle Bay Boots, with the same smooth leather uppers you'd expect from Timberland, but with lighter weight, extra grippy, and more comfortable sole construction. Ortholite insoles support your foot inside, and provide optimal moisture transport, for an ultra-breathable footbed that wicks away sweat to keep your feet cool and dry. Underneath the footbed, a triple-layer Sensorflex suspension system flexes with every step you take providing lasting comfort that adapts to uneven ground, providing you with smooth and stable support. The Eagle Bay boots come from Timberland's Earthkeepers line, which is designed with a commitment to the environment, using recycled and eco-conscious materials whenever possible. The outsoles are made from 34% recycled rubber, and feature a directional tread designed to grip and keep you moving forward with support in the front, and reverse directional tread in the back for braking power on steep hills.
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$159.95
Timberland Earthkeepers Rugged Originals Leather 6in Boot - Men's Timberland Earthkeepers Rugged Originals Leather 6in Boot - Men's
Explore our supposedly green planet wearing the eco-friendly, part-recycled Timberland Earthkeepers Leather 6in Boot. Leaving no trace is good, but if you want to help change industry practice as you traverse narrow strips of wilderness, get your feet in Timberland's Earthkeeper series.
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$149.95
Timberland Earthkeepers Rugged Waterproof 6in Plain Toe Boot - Men's Timberland Earthkeepers Rugged Waterproof 6in Plain Toe Boot - Men's
Just like your charming smile and rugged good looks, the Timberland Men's Earthkeepers Rugged Waterproof 6in Plain Toe Boots are versatile and classy. The waterproof full-grain leather upper remains durable and refined after each use, even if your daily routine involves roughing it at the ranch or campground. With recycled materials in the lining and sole, you help the environment while you rock it at a music festival. And since you're always on the go, it helps that the Earthkeepers have a waterproof membrane, lace closure, and insanely comfy padded collar.
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$179.95
Timberland Grantly Chukka Shoe - Men's Timberland Grantly Chukka Shoe - Men's
Timberland's Grantly Men's Chukka Shoe is durable and obviously handsome, but it's harder to recognize the recycled PET polyester mesh lining and laces unless you already know about them. While the full-grain leather and suede upper keeps you looking good, the OrthoLite footbed will make sure your soles and arches feel like a million bucks, and the self-cleaning rubber sole will help you stay solid on slippery sidewalks all over town.
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$119.95
Timberland Heston Mid GTX Boot - Men's Timberland Heston Mid GTX Boot - Men's
Lumberjacks don't take their boots lightly, and while Timberland didn't make the Heston Mid GTX Men's Boot specifically for tree fellers, it was inspired by them. Accordingly, the full-grain leather upper is supple, durable, and completely classic, and the Pendleton wool lining keeps your feet warm and comfortable whether you're laying in wood for the winter or sipping whiskey by the fireplace. Timberland also outfitted the Heston with a waterproof Gore-Tex membrane that'll allow you to stomp through snow and cruise through puddles without getting your feet wet. A cushy OrthoLite footbed provides killer comfort, and the Heston's SensorFlex midsole and outsole instantly adapts to uneven terrain to help you keep your footing when you're seeing how long you can hold a hot coal in your hand without screaming like a little girl.
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$169.95
Timberland Icon 6in Basic Boot - Men's Timberland Icon 6in Basic Boot - Men's
The Timberland Men's Icon 6in Basic Boot has been providing rugged style and premium performance to people from all walks of life for years. Full-grain leather ensures durability and a classic look, and taped seams prevent water from working its way in through the cracks. Lightweight and low-profile Primaloft insulation keeps your feet warm when working through the winter, and anti-fatigue comfort technology helps you handle long hours on your feet. A steel shank running through the midsole provides support and helps the boot maintain its shape for years to come, and the burly rubber lug outsole gives you traction on rugged terrain and muddy ground. Whether it's for looks or function, look no further than the Icon when you want the best.
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$159.95
Timberland Icon 6in Basic Waterproof Boot - Men's Timberland Icon 6in Basic Waterproof Boot - Men's
From fall cleanup at the cabin to exploring city streets, the Timberland Men's Icon 6in Basic Waterproof Boots offer a classic look that's designed to hold up to wear and tear. Crafted with a seam-sealed waterproof construction to keep your feet dry, these boots feature a premium leather upper for comfort, durability, and timeless style. A padded collar surrounds your ankle for comfort whether you're chopping wood or touring museums, while PrimaLoft Eco insulation shields your feet from the cold and retains warmth, even when wet. With a rubber lugged outsole for traction and durability, these boots will keep you moving confidently for years to come.
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$149.95
Timberland Icon 6in Premium Classic Boot - Men's Timberland Icon 6in Premium Classic Boot - Men's
The Timberland Premium Classic 6in waterproof hiking boot is a tough, well built boot that's infinitely versatile. From working around the house to clearing the back 40 to day hiking with the kids, this waterproof 6in high boot will take as much of a beating as you can give it. Timberland guarantees this boot to be waterproof, keeping your feet dry and happy no matter what the weather or trail conditions. The rubber lug outsole provides excellent grip and traction, while the lined upper cuff seals out moisture and debris.
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$189.95
Sale Price: $132.96
Timberland Kendrick Side Zip Boot - Men's Timberland Kendrick Side Zip Boot - Men's
No stranger to danger, the Timberland Men's Kendrick Side Zip Boot is an excellent choice for projecting your internal rebel-without-a-cause sensibilities without quitting your job and going into full existential life-crisis mode. Rocking a side-zip for an easy in-and-out application, the Kendrick includes a 34% recycled rubber sole and an eco-friendly leather tanning process that accounts for a full 50% of the full-grain upper. Plus, the Kendrick includes anti-microbial OrthoLite insoles that resist the propagation of stinky bacteria, so you (hopefully) won't clear the room when you finally peel them off.
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$159.95
Timberland Killington Leather Hiker Boot - Men's Timberland Killington Leather Hiker Boot - Men's
Start killing it on the trail this fall in Timberland's Killington Leather Hiker Boot, with classic timberland vibes featuring a recycled outsole that captures extra comfort and support on the trail or the sidewalk. Full-grain premium leather uppers offer lightweight protection and breathability, and lace up snugly around your foot to keep you supported. A breathable mesh lining made from 50% recycled plastic bottles wicks away moisture to keep your foot cool, and is partnered with OrthoLite footbeds that provide all-day support while wicking away moisture so you stay dry. SensorFlex midsoles adapt with every step you take keeping your stride smooth through variable terrain.
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$129.95
Timberland Norwood Mid Waterproof Boot - Women's Timberland Norwood Mid Waterproof Boot - Women's
Transition from trail to town without skipping a beat in the Timberland Women's Norwood Mid Waterproof Boot. The Norwood Mid Waterproof Boot brings an upbeat vibe to your urban exploits and hiking endeavors with its vibrant color pops and streamlined shape. The boot's mid-top silhouette maintains stability when you're conquering rugged terrain, ensuring you don't roll an ankle on the trail. Rubber lugs underfoot provide unrelenting traction when you're treading across rugged terrain, much like an overland vehicle placed in four-wheel drive. Premium leather is fortified with a waterproof membrane, sealing out heavy rain, sopping-wet snow, and puddle splashes from dampening your fun outside. Metal lacing eyelets are included for lasting durability when you're subjecting this boot to everyday abuse.
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$109.95
Timberland Westmore Leather/Fabric Boot - Men's Timberland Westmore Leather/Fabric Boot - Men's
The Timberland Men's Westmore Leather/Fabric Boot brings sophisticated style and lightweight comfort to your everyday routine while maintaining that distinctive Timberland look that you know and love. A combination of leather and canvas puts a fresh twist on this iconic silhouette, giving it a look you can take from gritty streets to upscale offices. Its lightweight build, cushy OrthoLite footbed, and supportive Dynamic SensorFlex technology keep you comfy even when you're on your feet all day, and it's made with recycled materials and environmentally-friendlier leather to create a more sustainable fashion statement.
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$159.95
Sale Price: $119.96
Timberland Westmore Leather/Fabric Chukka - Men's Timberland Westmore Leather/Fabric Chukka - Men's
From commuting to work on casual days to weekends spent exploring new towns, the Timberland Men's Westmore Leather/Fabric Chukka combines lightweight comfort with rugged style. Crafted with a leather and canvas upper, these boots have a casual deconstructed that are ready casual wanderings or date nights in the city. Cushioned footbeds and a SensorFlex comfort system keep your feet comfortable, even at the end of a long day when you can't remember where you parked your car.
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$149.95
Sale Price: $112.46


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