How to wear Timberlands

Written By Bakes

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

( This article contains affiliate links meaning we may earn commission) 

Over the years what started as a work boot for construction workers has now turned into a fashion statement through the influence of hip hop music and street culture. The boot is one of the most recognizable footwear’s worldwide and I will be showing you the right way on how to wear timberlands.

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. In order to style these right and compliment your outfit we will examine different outfit ideas, things to do and most importantly things not to do when looking at how to wear timberlands.

To ensure the best look for your timberland boots make sure you follow this guideline and you will be off to a great start.


How to wear timberlands the right way

  • Outfit Ideas
  • Things to do
  • Things not to do
  • FAQ’s
  • Conclusion


Contrast/Statement Look

how to wear timberlands 1

By combining colours that are the complete opposite of each other on the colour wheel is what allows you to achieve this high contrast look.

Therefore since the Classic 6 Inch boot is beige, when combined with black or any dark colours such as navy this contrast/standout look can be achieved.

Style with a long coat or jacket, t-shirt and slim jeans all consistent with the same colour, ensure accessories such as belts also follow the same dark theme and then pair with the classic timberland boot for the best look.

Purchase Biege Timberland Boots Here 


Smart Casual Look

how to wear timbs

Have you wondered how to wear timberlands with the intentions of having a smart casual appearance? Look no further!

In order to get this look right ensure you have one formal item such as a chesterfield Jacket, plain t-shirt and slim jeans.

With this option the timberland boot compliments both looks as it allows you to look neat yet informal in style at the same time.

The idea is with the Jacket on you get the Smart Casual look and off you get the casual look.

Purchase Biege Timberland Boots Here 


Double Denim Look

When rocking a double denim outfit ensure you stick to the rules which are that darker shades should be reserved for jeans and lighter denim for shirts.

Then pair with timberlands to finish off the outfit and due to the different shades of denim, it will allow for the timberlands to compliment the outfit.

Perfect for most occasions while also allowing you to select from a variety of timberland colours such as beige, black or navy, the choices are endless with this outfit.

Purchase Black Timberland Boots Here 


All Black Look

how to wear timberlands 2020

An all-black outfit with black timberlands provides the ultimate clean and minimal look while still being fashionable.

Similar to the contrast look I mentioned above with the only difference being the selected colour of the timberlands, an all-black outfit is great for most occasions and can be accessorized should you want to add more personality to the fit.

Purchase Black Timberland Boots Here 


Casual Look 1

how to lace timberlands

Not only can the timberland boot be styled in many different ways but also can be styled with cargo pants which is a great alternative to jeans.

For a casual look pair the timberlands with cargo pants and a denim jacket or any other item of choice such as a flannel shirt, plain t-shirt, or bomber jacket.

This outfit is ultimately going to allow for maximum comfort while still having fashionable appeal since the timberlands work great with both jeans and cargo pants.

Purchase Black Timberland Boots Here 


Casual Look 2

How to wear Timberlands 2

The sweater and timberland combination is often time worn in the winter and fall for good reason. During these seasons we tend to dress up warm while not wanting to compromise on style therefore this combination is great.

Leather or suede timberland boots paired with jeans and a sweater creates a clean and casual look suitable for most activities throughout the day.


Purchase Rust Nubuck Timberland Boots Here 



Biker Look

how to wear timberland boots 3


The timberland boot demands the cool factor and so does the Biker Jacket, so what’s not to love about the combination, it only makes sense!

It’s common to see a biker jacket in black and would make sense to pair with black 6-inch timberlands, however, use this opportunity to try on different colour of timberlands and different colour biker jacket to really stand out from the crowd.


Smart Casual Look 2

timberland boots style

For the second smart casual look the formal item of choice will be a plain shirt.

As I mentioned before the timberland boot compliments the look as it allows you to look neat yet informal in style at the same time.

Therefore the formal shirt and timberlands will be great for evening attire.

Purchase Black Timberland Boots Here 


Long Coat and Timberlands

long coat and timberlands

One of the best things about the timberland boot is that not only does it work great with formal coats but can also be styled with casual outer wear intended for the winter season.

Puffy, parka or fish tail the timbs will style great with most long coats and is a go to style for residents who live in places that get very cold in the winter such as New York, London & Toronto.

Outerwear and timberland is the perfect combo

Purchase Biege Timberland Boots Here 



Things to do


Care for your Timberland

timberland care kit

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.

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

Buy Product Care Kit Here


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.


Don’t wear the boots with sweats

Can you wear sweats with timbs

You will notice in the outfit ideas section I have not included sweats as an option and for good reason.

The Sweats and Timberland combination always come across lazy and unsure of the look you’re going for, therefore its best to be avoided.

You don’t see many people doing this, need I say more?


Don’t wear the boots with shorts

timberlands with shorts                                                                                                                                                           (Image via

Again it should come as no surprise that I have not offered an outfit idea which includes timberlands and shorts.

Though the timberland boot is multi-seasonal it’s best to be avoided in the summer months, besides who wants to wear big construction boots in 90-degree weather.

Timberlands should be offseason from June-September



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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