Timberland just dropped a fall sale with up to 50% off — shop my 11 favorite styles now

Classic, stylish and comfortable. It doesn't get better than the Davis Square Chukka Shoe — especially when you can get a pair for almost half off. These are made of premium Timberland leather and have comfortable OrthoLite insoles.

These Timberland sneakers look super unique! Reviewers on Amazon have also praised these shoes for their supportive, comfortable design. So if boots aren't for you, some Timberland sneakers are worth considering.

These boots remind me a bit of Uggs, without the fur lining. They have an easy pull-on design with tabs at each side, a premium leather upper and comfortable OrthoLite insoles.

All the comfort and waterproofing of Timberland boots, but in an easy-on, easy-off lace-free design. Made with premium leather and with a soft Ortholite footbed, these are a must-buy addition to your wardrobe.

These bold boots can stand up to the challenge of a rainy day thanks to their waterproof seam-sealed construction. The boot is available in a variety of colors, although this light beige hue is one of the only options on sale. They feature a 4.6 rating with nearly 2,000 positive reviews, so I would grab a pair today!

If you've been looking for a pair of long black boots, this might just fit the bill. And $96 off won't hurt either. Timberland's great at making waterproof boots that keep your feet dry, alongside an anti-fatigue footbed which is a pretty cool addition.

These ankle boots offer versatility, function — and protection for the elements. Not only are they stylish, but they also have rubber lug outsoles for excellent traction and grip on slippery surfaces.

These Timberland Pro boot are perfect for tough workdays. They're equipped with Timberland's PRO 24/7 tech, which supports your feet and reduces fatigue. Steel toe caps and electrical hazard protection are on board, too.

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.

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.

This is one of the more expensive Timberland styles you'll find, but these lined waterproof boots are well worth it and perfect for the colder months of the year. Their grippy platform soles will keep you steady in less-than-ideal conditions and the soft lining adds warmth.