Timberlands: Perfect for Hiking, Fashion, and Every Day Timberlands: Perfect for Hiking, Fashion, and Every Day

The Best Timberland Boots for Fall — from the Classic 6-inch Pair to the Best Collabs

You can’t talk about boots for the fall without mentioning Timberland. As one of the few outdoor brands to transcend its own utility, Timberland boots have been a mainstay of both the fashion crowd and outdoorsy types alike. Whether you’re shopping for a rugged hiker for adventures, a comfortable boot for daily wear, or a unique fashion-forward collaboration, Timberland has it.

I’m a sneaker collector at heart, but I own at least 15 pairs of Timberland boots. The 6-inch Premium Boots in wheat are always in my fall rotation, and I absolutely love the Super Boots for harsher weather. Previous collaborations like the Aime Leon Dore 7-Eye Lug Boot also appeal to my senses as a collector. If I wasn’t such a fanatic for the brand, I’d be content with one or two pairs because they’re so well made.

The 5 best classic Timberland boots for fall:

Although Timberland boots are a style staple, all of its designs are built on the brand’s history as an outdoor supplier. Almost every boot Timberland makes is waterproof, warm, and constructed with durable materials.

And, though the brand doesn’t do much to advertise it, they’ve been in the sustainability game long before it became a trend in the footwear industry. The brand uses recycled plastic interior linings and laces, recycled rubber outsoles, and ethically sourced leather uppers from silver-rated tanneries on a majority of its shoes.

If you define your fall style as classic, a pair of 6-inch boots in black or wheat might be the best choice for you. If you plan on hitting the backcountry this fall, but still want to look good on the street, the Timberland Fly Roam Trail Mid is a capable and versatile boot.


Generally, Timberland boots run slightly big, so I usually go down half a size. If you do choose your true size and they’re roomier than expected, you can always pair them with thick wool socks for cozy warmth. With most pairs priced at $140-$240, Timberland is one of the most affordable boot brands that I’d recommend when you take into consideration how well they’re made. Regardless of which pair you pick, you’ll have them for years to come.

The 6 best Timberland collabs and new silhouettes for the fall: