Massive Timberland boot and apparel sale from $19 — 21 deals I’d shop right now

Timberland Deals
(Image credit: Timberland)

Rugged and stylish rarely go hand-in-hand — except for when it comes to Timberland, the footwear and apparel brand best known for its iconic yellow work boots. Whether you're looking to add some casual workwear or trail-ready pieces to your spring wardrobe, you've come to the right place.

Timberland is currently hosting an end-of-season sale with deals on boots, hiking shoes, outerwear and more that will help transition you into spring. Additionally, you can find select Timberland styles for both men and women on sale at Amazon.

With sturdy boot options and comfortable apparel deals starting at just $19, I recommend shopping these items ASAP. Below, I've rounded up my favorite Timberland sale styles.

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Best Timberland Apparel Deals

Timberland Linear Logo Short Sleeve T-Shirt (Men's)
Timberland Linear Logo Short Sleeve T-Shirt (Men's): was $30 now $19 at timberland.com

Throw on this easy t-shirt featuring the Timberland logo. It's cool, comfortable and made of 100% cotton so you'll love wearing it all day long.

Timberland Utility Cargo Pant (Women's)
Timberland Utility Cargo Pant (Women's): was $80 now $29 at timberland.com

Sure, jeans are great, but why not add these unique cargo pants to your closet. They also feature the extra utility of signature workwear-styled pockets, so you can wear them to work or in your personal time.

Timberland Kennebec River Tree Logo Hoodie (Men's)
Timberland Kennebec River Tree Logo Hoodie (Men's): was $60 now $39 at timberland.com

Sport the Timberland logo proudly when wearing this bold hoodie. Available in several different colors, the sweatshirt is made of cotton and offers the perfect amount of warmth.

Timberland Tempe Jogger Pants (Men's)
Timberland Tempe Jogger Pants (Men's): was $70 now $59 at timberland.com

These joggers work almost as hard as you do! Featuring light, durable flex fabric for comfort, these joggers will be your go-to pair this season and beyond, whether you're on the job or on the go.

Timberland Strafford Quilted Washed Canvas Jacket (Women's)
Timberland Strafford Quilted Washed Canvas Jacket (Women's): was $149 now $59 at timberland.com

Made with 100% recycled cotton fabric, this ultra comfortable canvas jacket is the perfect lightweight option as the weather gets warmer.  Pair this with any top and pants for a casual-yet-elevated look. We're also loving the color for spring.

Best Women's Timberland Boot Deals

Timberland Skyla Bay 2.0 Mid Warm Lined Sneaker (Women's)
Timberland Skyla Bay 2.0 Mid Warm Lined Sneaker (Women's): was $90 now $39 at timberland.com

Want some sneakers that keep your feet warm? The Skyla Bay 2.0 does the job. They have a leather outer with have a faux fur collar and lining. Plus, the stretch panel at the side makes them easy to put on.

Timberland Ellendale Mid Lace-Up Boot (Women's)
Timberland Ellendale Mid Lace-Up Boot (Women's): was $100 now $49 at timberland.com

These trail-ready boots are the perfect pick if you're heading outdoors. The uppers are made of premium leather and durable polyester and they're also water-repellant, so they'll look good longer. Not only did they receive a 4.5 star rating online, but one happy customer mentions, "They are so comfortable right out of the box and I get so many compliments on them."

Timberland Chocorua Tall Lace-Up Waterproof Snow Boot (Women's)
Timberland Chocorua Tall Lace-Up Waterproof Snow Boot (Women's): was $170 now $69 at timberland.com

Hoping to head out into the snow? Gear up for the winter weather in these lace-up waterproof snow boots that are stylish, comfortable and warm — a triple threat if you ask me!

Timberland Greyfield Mid Lace-Up Boot (Women's)
Timberland Greyfield Mid Lace-Up Boot (Women's): was $130 now $79 at timberland.com

A work boot with a contemporary design, these surprisingly lightweight boots are packed with benefits like leather uppers and a fabric lining containing at least 50% recycled plastic. Additionally, the boots are stylish, dependable and durable.

Timberland Brimfield Mid Chelsea Boot (Women's)
Timberland Brimfield Mid Chelsea Boot (Women's): was $150 now $89 at timberland.com

Built to be comfortable, durable and of course, stylish, these Chelsea boots are perfect for every day wear. They feature all-day cushioning, support and a custom fit. Plus, their sturdy rubber lug outsoles are designed to provide all-weather traction.

Timberland Stone Street Mid Lace Up Boot (Women's)
Timberland Stone Street Mid Lace Up Boot (Women's): was $140 now $101 at Amazon

These Timberland boots have a classic look that's super stylish. They have a leather upper and an OrthoLite Impressions memory foam footbed that'll feel like you're walking on a cloud.

Timberland Allington Heights 6" Boot (Women's)
Timberland Allington Heights 6" Boot (Women's): was $150 now $119 at Amazon

These Timberland boots take your style to new heights! These are made of premium Timberland leather and are as comfortable as can be thanks to their memory foam footbed.

Timberland Everleigh Mid Chelsea Boot (Women's)
Timberland Everleigh Mid Chelsea Boot (Women's): was $160 now $140 at Amazon

Timberland's Everleigh Mid Chelsea Boot joins Amazon's sale lineup! Right now you can get them starting from $140. These pull on with no laces and are super stylish. Plus, they have a memory foam footbed to keep your feet comfortable.

Best Men's Timberland Boot Deals

Timberland Chillberg Waterproof Insulated Boot (Men's)
Timberland Chillberg Waterproof Insulated Boot (Men's): was $150 now $49 at timberland.com

Let's face it: the winter can be harsh. That's why you need a boot that can help protect you from the elements. You’ll want this rugged, waterproof and insulated Timberland boot that's designed to be durable through hours of cold conditions, while helping your feet stay warm and dry.

Timberland Gritstone 6" Steel Toe Work Boot (Men's)
Timberland Gritstone 6" Steel Toe Work Boot (Men's): was $125 now $74 at timberland.com

Durable, rugged and built to protect in many different environments (including electrical hazards), this steel safety-toe work boot is the ideal pick if you're looking for a comfortable boot to wear all day long. The boots feature an abrasion-resistant rubber outsole using cement construction for flexibility and a breathable, moisture-wicking mesh lining.

Timberland Mt. Maddsen Mid Lace-Up Hiking Boot (Men's)
Timberland Mt. Maddsen Mid Lace-Up Hiking Boot (Men's): was $110 now $79 at timberland.com

These Timberland hiking boots are perfect to keep your feet protected on the trails. They have tough traction outsoles and an EVA midsole for comfort. Only a few sizes are left in stock, so get these while you can.

Timberland Flume Mid Waterproof Hiking Boot (Men's)
Timberland Flume Mid Waterproof Hiking Boot (Men's): was $115 now $89 at Amazon

These Timberland hiking boots will help you take on the elements thanks to their waterproof design. The hardware is also rustproof and their EVA midsoles support your feet.

Timberland Converge Mid Lace-Up Waterproof Boot (Men's)
Timberland Converge Mid Lace-Up Waterproof Boot (Men's): was $160 now $89 at timberland.com

Whether you're on or off the trail, you can feel confident with the waterproof boot that was designed for grip and crafted with sustainable materials. Another 4.5 star option, one reviewer wrote, "I wore them fishing and hiking and immediately felt like they were designed for my feet. Very comfortable and very true to size."

Timberland Mt Lincoln Mid Lace-Up Waterproof Hiking Boot (Men's)
Timberland Mt Lincoln Mid Lace-Up Waterproof Hiking Boot (Men's): was $170 now $99 at timberland.com

The perfect boot for when there's unexpected weather on the mountain, the Mt. Lincoln hiking boots feature the finest waterproofing materials and technology, as well as 200 grams of insulation designed to maintain warmth, even when they get wet.

Timberland White Ledge Waterproof Mid Hiker Boot (Men's)
Timberland White Ledge Waterproof Mid Hiker Boot (Men's): was $120 now $99 at Amazon

A no-brainer for your next outdoor adventure, this hiking boot is built with waterproof premium leather and features seam-sealed construction to protect against the elements. Plus, they have a rubber lug outsole for traction on the trails.

Timberland Newmarket Mid Lace Up Fashion Boot (Men's)
Timberland Newmarket Mid Lace Up Fashion Boot (Men's): was $150 now $122 at Amazon

Amazon has slashed the price of these Newmarket boots from Timberland. Available in three different colors, these are made of leather and have a durable rubber outsole.

Olivia Halevy

Olivia is a Deals Writer at Tom’s Guide. She loves all things lifestyle, shopping, and sourcing the best deals from some of the top brands, retailers, and websites around. From fashion and beauty to smart home and tech, she has an eye for finding practical, stylish, and reasonably-priced items that help make life simpler (and a little more aesthetically-pleasing). Olivia has over five years of experience writing lifestyle, commerce, and branded content for Patch.com. In her free time, she enjoys trying out new exercise classes, binge-watching the latest viral TV shows, cooking, spending time with family, and taking long walks with her dog, Gus. 

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