My favorite pair for the rigors of winter

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  • I own dozens of boots from many brands, but the Timberland Super Boot is my favorite choice for winter.
  • The brand has just reissued the great boot in its most iconic and collectible colourway.
  • Here’s what they like to wear and where you can buy them.

I got my first pair of Timberland boots when I was in kindergarten. It was 1998 and I was only five years old, but I vividly remember those classic six-inch Wheat boots being my favorite shoes back then. Over the years I’ve worn a handful of other Timberlands – and I’d probably still have a majority of them today, if I hadn’t outgrown them.

Twenty-four years later, my feet have stopped growing, so I don’t have to replace my shoes as often. When buying boots now, I’m looking for build quality that can last a lifetime – and Timberland is still, without a doubt, my number one choice.

Of the over 20 pairs of Timberlands I own, the Super Boot is by far my favorite silhouette due to its longevity in quality and style. I currently own seven pairs of Super Boots, including the most iconic color, “Hazel Highway”, which the brand just brought back.

Timberland Super Boots

Amir wearing the 2016 reissue of the Timberland Super Boots.

Amir Ismael / Initiate


Originally released in 1979, the Timberland Super Boots were designed for Alaskan commuters and hunters who need footwear that is durable, waterproof, and warm for long periods of time. Often called the Iditarod boot for its popularity among Alaskan dog sled racers or the 40 Under boot for withstanding -40° Fahrenheit temperatures, they have a solid reputation for cold weather wear.

While the Timberland Super Boot proved its worth in cold weather, the boot also became a winter street style staple after being popularized in the 1990s. Unlike other Timberland styles like 6-inch Boots, the Super Boots are not always available. After being absent for many years, they have seen recent releases in 2016, 2019 and now 2022. Each time they return, the release is special for fans of the iconic boot.

What Super Boots Look Like

The Timberland Super Boots feature an eight-inch height, the iconic dark brown leather upper, rust-resistant lace hardware, 200 grams of Primaloft insulation and Vibram outsoles.

Although I have never been to Alaska or set foot outside in sub-zero temperatures, I have worn my Super Boots countless times during the harsh New York and New Jersey winters. Even with normal socks, I was able to comfortably stand outside without getting frozen toes.

Leather uppers are incredibly durable and easy to maintain. In the five years I’ve owned this pair, I’ve only wiped them down with water when they got dirty and they haven’t been scuffed or discolored. The Vibram soles are just as durable and show virtually no signs of wear.

nutty highway

Timberland Super Boots provide exceptional warmth and traction in the snow.

Amir Ismael / Initiate


Disadvantages to consider

The only possible drawback of the Super Boots is the weight. They’re pretty heavy, but that’s something you should expect given its eight-inch height, thick leather upper, and sturdy Vibram sole. If you’re less concerned with the iconic style and really need lighter boots, Timberland has plenty of modern models in the GreenStride collection that are incredibly lightweight, yet durable and warm.

The bottom line

At $260, the Timberland Super boots are an incredible value. Although I already have several pairs of dark brown Super Boots, my first pair is in such good condition that I had no reason to wear the others. They last a very long duration.

If you’re not a shoe collector like me, you can buy a pair and not have to worry about replacing them for many years.

Whether you’re into classic ’90s street style or extreme heat, the Timberland Super Boot is a great choice. If you’re looking for winter boots that will last a lifetime, you’ve just found them.

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