Timberland Boots Outfit Gallery (Unisex Options)

Written By Bakes

Avid writer on Men's Hair, Grooming, and Lifestyle!

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Due to the fact that the Timberland boot is multi-seasonal, it can be styled in many different ways which include winter, spring and fall outfits.

Our editorial serves as a comprehensive guide and gallery for both men and women to explore different styling options.

Dungarees & Timbs

Channel your inner 90s Aesthetic with this classic fit!
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Rugby Polo Shirt Outfit

Rugby Polos paired with Timbs takes us back to the days of a young Kanye West! The look is yet to be phased out!
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Summer Alternative Outfit

Channel your inner Aliyah with this 90s summer Outfit
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90s Baggy Outfit

Back to the days when Streetwear was Baggy and Jeans covered Timbs
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Puffy Jacket with Timbs Outfit

Winter Timberland Boots Style? Covered!
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Sweat suit Outfit

Sweats and Boots! The Perfect Errands Run Combo
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Worker Outfit

The original way Timbs were worn! Worker Outfit Style.
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Winter Inspired

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Spring Casual

Our favourite alternative Color to the nubuck leather – RUST!
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Double Denim

Going for a Double Denim Look? Then contrast the outfit with the classic Nubuck Leather
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Leather Jacket Timbs Outfit

Black Leather Jacket? Only makes sense to bring out the Black Timbs!
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Preppy Fashion Outfit

Who said you could only pair a preppy outfit with formal shoes? Move over Penny Loafers!
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Spring Casual Outfit

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Things to do

Care for your Timberland

timberland care kit

By investing in a product care kit you’re sure to protect your Leather, Suede, Nubuck & Fabric timberlands against water and stains.

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Yes they are waterproof, and by waterproof what timberland is suggesting is that the boot is designed in such a way that in wet weather conditions the boot won’t allow your feet to get wet, however, the long term effects on suede leather will start to show therefore it’s important that you make sure you care for your timberland boots.

Make sure the tongue of the boot is upright

It pretty much goes without saying that the lifeline of a timberland boot is in the tongue so ensure your jeans fall behind it always.

Until timberland sorts out new technology into the boot which will hold the tongue upright for longer periods of time it’s within your best interest to assume they will probably start to fold sooner than later. With this mentality, it will probably influence you to care for the boot for much longer by lacing up the tongue and for a better look ensuring denim falls behind the boot’s tongue.

An old tongue that no longer will sit upright is good enough to be thrown away.

Get the Right Size

timberland size

Make no mistake by assuming the timberland boot fits just as your regular sneakers do.

The boot is big, which is why you need to make sure you get the right size, especially if you plan to wear your laces loose.

The best course of action is to check out the official timberland boot sizing guide and if you’re still unsure just head down to the nearest store and try on a pair, you will get the best size in doing so.

Things not to do

Don’t Lace to tight

So you’re thinking about how to wear timberlands to look cool? Well, remember don’t lace them to tight as it kills its initial appeal while looking nerdy.

Ensure the right amount of tightness without losing the cool look.

Naturally construction workers on-site would lace the boot tightly for safety reasons. Once it was adapted by hip hop the laces got looser and became the benchmark of cool.

FAQ’s

How long does it take to break in Timberlands?

From our experience it can typically take a month to break into timberlands. To achieve a faster result ensure you are regularly wearing the boot. Aim for 3-4 times a week.

What pants go with Timberland boots?

For the best results timberland work best with denim jeans. An alternative to this are cargo pants however jeans are your best option.

Can you wear Timbs all year round?

The short answer is yes. Timbs can be worn all year round, however, due to it being a boot it may better to opt for sneakers in summer. Timberland boots are best for winter, fall and spring seasons.

Are all Timberland boots waterproof?

The vast majority of timberland boots and shoes are waterproof. Timberland is known worldwide for its shoe being durable. Waterproof range here

Do timberlands last?

With the right care and attention, Timberland boots can last for years. The boot has been designed with waterproof leather, quality stitching and hard soles.


Since the timberland is multi-seasonal it means there are a variety of styles to be explored when it comes to wearing the boot.

The boot is already a classic and most of the work has been done, now it’s your job to add your signature style to compliment it.

Hopefully, you now know how to wear timberlands the right way, find out how to wear your Nike air forces! 

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