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For years now, I have been eyeing Timberland boots. Coming from the world of unforgiving Dr. Martens, Timbs always seemed like a comfortable, practical alternative that would keep my feet dry through winter slog and wouldn’t require two years of blisters to break in.
Yet I always felt a little hesitation buying the OG Timberland workboots, even though they come in so many fun colors. As someone with a desk job, I try to be cognizant of appropriating utility workwear. Plus, the classic style reminds me of the boys I went to high school with, who also probably didn’t do manual labor, but nonetheless wore steel-toe boots to Algebra 2.
It’s safe the say the boot gods blessed me this fall when the brand released a platform version of these classic kicks. They have all the pros of the trademark style — they’re waterproof and insulated with a memory foam footbed, and they lace up with a little cushion around the ankles for extra support — but this pair also has a stylish, two-inch thick platform sole that gives the boot a chunky ’90s feel.
These are exactly the Timberlands I want to be wearing, so I immediately got a pair in the iconic warm tan nubuck. The thick heel looks more natural on my foot and in line with my daily style. I don’t feel like I’m trying to be Bob The Builder when wearing them, I just feel really comfortable and cool.
I’ve had my pair for a few months now and have been wearing them consistently when doing street outreach with the harm reduction group I volunteer with, meaning I’m outside and on my feet for hours at a time. They’re perfect for walking long distances or standing for long days, as they’re not heavy or bulky but give a ton of support through your foot and ankle. They felt great right out of the box and are very easy to spot clean, though I like the look of them getting more worn in and weathered.
Also, if you’re walking in gross weather, around mud or just nasty city slush, the platform keeps your foot higher from it all while still giving strong traction. I never worry about stepping in a puddle or slipping on something, and get an almost child-in-a-puddle-like joy from stomping about.
I opted for the classic light brown leather because I like that it looks like an exaggerated, almost campy version of the classic Timberland. But if you’re looking for a non-descript chunky combat boot look, I recommend the all-black versions in nubuck and a super chic full-grain. If someone saw you wearing them on the street, they may not even know they were Timbs until you bragged about your warm, dry, comfortable feet. These would make ideal winter shoes to wear to the office or dinners or events in the cold — they’re super easy to dress up, would look great with dresses, skirts or trousers, and give you a little height but still keep your feet protected and cozy.
The red and dark green version also don’t scream “work boots” to me and look a lot more warm and folksy, kind of the same energy as Blundstones but with a lace-up detail. They’d pair great with blue jeans or cargo pants, whether you’re running errands, spending time outside or just running around the city on a chilly morning.
If you’re in the market for a pair of comfortable, waterproof, warm winter boots that are actually stylish and can be worn out and about and even while shoveling snow, these are the ones for you. They’re a retro take on a timeless style that makes them a little more inviting and easy to mix into your warm-weather wardrobe.
“Loving the boots. They are great for the winter and of course love the platform it has. This shoe is very comfortable to walk in and the material is chef’s kiss” — Jade
″It is so comfortable to wear daily. True to size. Highly recommended for those who are looking for a comfy boot to wear in winter.” — Y
“Highly recommend, soft insole, very warm for the cold season, perfect weight, not heavy and not super light.” — Yevheniia
“Great warmth and comfort with this boot. The sole is super sturdy. Definite recommend!” — Ellen
“These boots are officially a fall staple in my closet! They’re so comfortable, I could wear them for hours. They’re also flattering for the fall season, and I will be reaching for these shoes first for the next few months!” — Zelda
“Love these. Very cute and chic. These are so comfortable and easy to walk in. I’ve used them to run errands, shop around at a mall, and “hike” on flat ground. They held up well even though it was muddy and rainy. Definitely recommend” — Xena11