Timberland offers some of the world’s most popular casual boots. But, with their popularity, it raises the question: Are they really worth it?

History of Timberland

Timberland’s history begins in 1952, when its founder, Nathan Schwarz, bought a 50% stake in a company then known as the Abington Shoe Company. He then turned the company into a private family business and relocated to New Market, New Hampshire, though the employee headquarters now reside in Stratham. The area is well known for its outdoorsman lifestyle and somewhat temperamental weather, being similar in climate to Maine, home of the LL Bean Duck Boot.

Abington Company boots were originally intended to be durable outdoor footwear that could be stylish while still enduring the elements of an outdoorsman’s lifestyle. In 1973, the company released its iconic, yellow, waterproof boots under the model name “Timberland.” It quickly became a hit with outdoorsmen and tradesmen alike; so much so the company rebranded to just “Timberland.”

Iconic TIMBERLAND

Yellow Boots

These boots were originally widely accepted by factory workers and construction workers as working-class boots. However, Schwartz thought the sleek styling would appeal to higher-end clientele as more of a fashion staple in the luxury space. The boots were marketed in the New Yorker magazine and New York City’s Saks 5th Avenue, soon making them a symbol of relaxed luxury.

These boots reached mainstream success when Biggy Smalls mentioned them and his hit single “Hypnotize” in 1997. We tend to wear Timberlands more often than the Coogie sweater trend he also popularized, so everyone became hypnotized by their streetwear appeal. So much so that the New York Times reported flight attendants would buy them in bulk and then sell them in Milan at double the price.

“Timbs for my hooligans in Brooklyn”

Hypnotize by Biggy Smalls

They were later permanently featured on shows like “One Tree Hill.” Soon, other celebrities like Jay-Z, Nas, Kanye West, Mark Walberg, and Rihanna adopted the boot within their fashion trends and are especially popular among hip-hop communities, and they’ve remained a streetwear staple since.

Timberland’s Ethos

Timberland markets itself as the tough and dependable brand that makes hard-wearing boots with an outdoorsy appeal but urban enough design that they won’t look out of place when not worn hiking. They’re more often known for their stylish looks nowadays than their actual practicality, meaning that they’re closer to a fashion boot than their working boot origins.

The company’s ethos focuses on sustainability and positive change. This is done through humanitarian work when addressing the public. For example, they use recycled plastic bottles to make the soles of some of their footwear. They also focus on donating to tree planting causes in needed areas through community service and giving back to tradesmen through scholarships, making them a very environmentally conscious company working toward a greener world.

Timberland is also more worn as a lifestyle brand, unlike Redwing, which is largely intended as a work boot. It seems like more of an aesthetic choice, making them more desirable and aspirational to those who want to emulate the image they crafted during the 90s.

Timberlands have also gained recognition on the global scale as an international import brand. They have a reputation as something of a luxury and a flex item in both Europe and Asia, with their popularity being especially prevalent in the UK and Japan. This is probably due to the number of American celebrity endorsements they get, making them a sought-after piece for those looking to emulate the look.

Their aesthetic will mostly cater to trade workers, outdoor enthusiasts, fans of hip-hop aesthetics, creative hipster types, streetwear enthusiasts, and urban chic stylists. That being said, it’s no surprise that these boots will have limited capability within Classic Style as it’s an extremely casual boot, meaning that it’s probably not a great option for your suits or sport coats. However, that’s not to say that you can’t wear them in a classic manner.

They’ll be most at home with denim and flannel shirts but can also work with timeless classic items like leather jackets, denim jackets, chinos, or even suede jackets. But there’s no denying that they’ll be most at home if you’re cultivating a streetwear or urban style.

Timberland Boot Lines

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This is the company’s flagship product. Its most iconic features are the nubuck leather upper and leather strip around the padded collar of the heel. The leather has been waterproofed and insulated and features a natural rubber lug outsole.

FLAGSHIP BOOT

Cement Welted?

The most disappointing feature is that these boots are cement welted, instead of Goodyear-welted, meaning they likely have a lifespan of four to five years with regular use, unlike a Goodyear counterpart that can last 20 plus years when the sole is changed out after heavy use, and the upper is consistently cared for. Ironically, this goes against Timberland’s sustainability ethos, as the boots will have to be replaced more frequently and use more materials over time.

The most iconic color is the dark wheat or yellow style boot. Ironically, this coloring does show more dirt on them when worn for outdoorsman activities. They also come in black, gray, and more unusual colors like purple.

Available in sizes 6 to 18 in the USA with narrow, medium, and wide widths, they are listed as fitting true to size. The Premium Style is around $210, but often goes on sale for $150, a fairly hefty price tag for a more fashion-oriented boot.

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This style is more of a hybrid between a sneaker and a boot, featuring an outsole more in line with the tennis shoe. They still feature the nubuck upper of their mainline counterparts and come in at $150.

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The Redwood line features a thinner outsole; it is more in line with being worn in an urban environment, making it a more streetwear-friendly version of the boot, and it comes in at $145.

True Hiking and Field Boots

Timberland also features more true hiking and field boots, but those are more utilitarian in design and not made with the purposes that we really focus on here at the Gentleman’s Gazette.

Our Review

Here, we are reviewing the Timberland Premium 6-in Waterproof Boot in classic wheat nubuck. It features microfiber PrimaLoft insulation, a molded foam footed to reduce shock and improve comfort, and is made from premium Timberland leather. However, that term is primarily defined relative to environmental impact and not leather quality. We bought these ourselves for $198, and, like all of our reviews, this is not an ad.

Here is what Kyle had to say:

PREMIUM MATERIAL

Good Quality Leather

The boot looks great in person. I really enjoy the feel of the leather; doesn’t feel overly heavy or too light and thin. It feels like a great weight. The quality of the material seems great. I really like the feel of the leather behind the ankle. It’s very comfortable, but I don’t feel like I’m touching or feeling a cheap kind of plastic-looking boot. It definitely feels like there is some good-quality material in use here.

The sole does look sturdy, and it definitely doesn’t feel like we’re going to have anybody slipping or falling too easily. It’s got a great structure and a good thickness to it, so you should have a pretty easy time walking around and functioning through different weather conditions as well.

Personally, feel like these boots would hold up for a lot of different wears. I think it all depends on the person and what they do in their day-to-day life, of course, but I definitely feel like touching it, feeling it, putting it on, that these are going to last you a healthy amount of time.

The initial experience when putting on the boots is quite comfortable, but it certainly feels like I might need to break them in a little bit. I have slightly wider feet, but I could handle this regular width just fine, and I think, after breaking them in and wearing them with some thicker socks, it’s totally going to be fine. It is very comfortable for multiple wears over time. I don’t necessarily feel like the boot is running too small or too big. It seems quite average, so pretty true to size, is what I would say.

The boots don’t feel exceptionally heavy like some of my RedWing boots, but again, they don’t feel very cheap and lightweight like they’re made from plastic. So, it’s a good medium weight. There’s some pep to it, but not aggressively too heavy or too uncomfortable on your feet. I feel like the lug outsole does improve traction to a point.

Would I consider this an all-season boot? I can definitely see it more of a three-season boot for me, personally, but there are people out there who just love the style that much and would probably want to wear it any time of the year—all twelve months.

The Lighter color

Shows Dirt Quite Easily

The color is lighter, and I can definitely see how dirt and different things on here would show up a little bit easier and look dirtier faster, but I think, again, it kind of plays back into what your day-to-day lifestyle is.

If you’re someone who’s very cautious about where you step and as you’re moving throughout the day, you’re probably going to be fine with minimal spots or dirt on there. If you’re wearing these for more outdoorsman activities—hiking, things like that—you’re probably going to see much more smudges and dirt on your boots that much faster, so the color will allow it to be seen a little bit more. But I think it also kind of plays into what you’re going to be doing throughout your day.

I personally feel like I can adapt these boots into my classic style or my version of classic style because I like to mix things up a little bit and try different styles that might lean more casual sometimes. So, for me, I think it’d be okay.

For some people, it might not be their thing to do. They might want to go for a more dressy boot for the way they want to manipulate their outfits, but I think, for me, I could probably incorporate them with certain outfits and not deviate too much out of classic style with the rest of the outfit, so I think I can make it work. I think that there’s some great cost-per-wear and, personally, I think I would buy these shoes myself.

Comfort, style, the fact that they can be incorporated into different parts of my wardrobe, dressed down into classic style a little bit as well; these things appeal to me.

Conclusion: Is it Worth It?

For that reason, I would certainly buy these boots. At $210, there are brands and similar price points that offer a Goodyear-welted or Blake-stitched product, like Allen Edmonds, Taft, Thursday Boots, etc. If construction methods are important to you and you like your boots to last longer, these would usually be the better options to go for.

That being said, Timberland does have a signature boot style that no one else does quite as well. They’re probably not the most optimal choice for workwear or for hiking, as you’d be better off using more utilitarian boosts instead—something specifically designed with hiking in mind.

They can be serviceable for this purpose; if you really want to wear them for more leisurely outdoor activities, they’re truly best used as a fashionable piece within street and casual wear with their unique aesthetic and casual reputation.

They’ve also stood the test of time for over fifty years, being a style still popular today, meaning that they do have a timeless appeal for their intended purpose, even if it’s not what we usually have in mind when talking about classic style as their limited versatility and casual nature will make them fairly incompatible with a more formal wardrobe. But, if you have a more casual, street wear-oriented style, these boots could be appealing. Just know you’re paying extra for the brand name and style and not necessarily because it’s the highest quality product on the market; although the market price isn’t as drastic relative to actual value as other name-brand footwear have been.

What are your opinions of Timberland boots? Let us know in the comments if you own a pair and if your opinions match ours.

Outfit Rundown

Fort Belvedere

Midnight Blue and Burgundy Shadow Stripe Ribbed Socks Fil d'Ecosse Cotton

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Roberto Ugolini

Derby – Roberto Ugolini Fragrance

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Today, I’m wearing a green vest, a blue and white striped button-down shirt, green trousers with Fort Belvedere socks, and Timberland boots. My fragrance today is by Roberto Ugolini Derby. Check out the Fort Belvedere shop here for socks like these.