How To Wear Timberlands

When you’re shopping for a new pair of iconic boots—if you don’t already have them in your clothing arsenal—there are two things you should consider. First, you must think about how you’ll style them and second if you’ll be able to pull them off. And this is especially the case when styling your Timberland boots.

Most likely, you put effort into choosing your outfits and there’s a specific vibe or look you’re trying to achieve. You probably don’t just throw your outfit together without thinking about it (and we don’t recommend that). 

That’s because, without careful thought, you could end up with a look that you’re not happy with. And if you’re trying to style Timberland boots, this could be a fashion disaster.

For instance, you might have plenty of jeans and flannels in your wardrobe, but if you pair your flannel top with jeans and Timberlands, your outfit would look a little too lumberjack-y and Halloween is only one day a year (unless you’re actually a lumberjack). Then you can wear your Timberlands, flannel, and denim all year round.

Fortunately, we’re here to help show you how to wear Timberlands so that you’ll look great each time you put them on. And with our helpful tips and tricks, you’ll avoid any fashion faux pas. After reading through our guide, you’ll know:

  • How to style Timberland boots
  • How to create a specific vibe
  • Which Timberland boots work best with your aesthetic
  • What to avoid when styling them
  • Tips and tricks to keep your Timberlands looking like new

What are Timberland Boots?

If you’re not 100% sure what Timberland boots actually are, no worries. We’re about to enlighten you.

Timberland work boots are a very common, classic footwear, and there’s no doubt you’ve seen a pair if you’ve ever hired a contractor or been on a construction site yourself. That’s because construction workers tend to wear these practical boots often.

Timberland boots are crafted from thick, waterproofed leather and feature a classic work boot design. They come with a thick and durable rubber sole that can handle all terrains. Plus, they often have a high-top design that’s both protective and functional. The super-soft upper material and comfortable fit make these boots stylish, unique, and loved by many. 

It’s also important to keep in mind that there are Timberland boots for men and for women with a range of different styles, fits, colors, and shapes. So, there’s an option for everyone who wants to get their hands on a pair.

History of Timberland Boots

Now that you know a little more about what Timberland boots actually are, you might be wondering about the brand’s history. The Timberland Company dates back to 1952 when Nathan Swartz purchased Abington Shoe Company with his business partner. He moved to the US, bought out his partner, and turned it into a family-owned business. 

Fast forward 20 years later and the original Timberland shoes were invented. They were a waterproof work boot with an iconic yellow hue. Of course, the unique weatherproof design quickly became popular and workers, outdoorsy folk, and everyone who ever needed a good pair of shoes flocked to the store. 

As times have changed, these boots haven’t changed that much. Over the years, the original idea behind the boots has stayed the same. They’re still made with a high-quality design and careful craftsmanship, which is why they’ve stood the test of time. It’s also why, after all these years, they’re still just a good ol’ pair of shoes. 

Adding some innovative styles, silhouettes, and different design ideas to their product line, the brand has only continued to skyrocket and remains a tried-and-true choice in the footwear industry.

When to Wear Timberland Boots

After learning some info about Timberland boots, you may be wondering when to wear these shoes. When’s the best time to wear them, you ask? With their thick leather material and waterproofing, they’re definitely an ideal option for the cooler (and wetter) months. And, of course, they make a great work boot. 

On top of that, the brand offers some pretty stylish options for casual everyday wear—whether you’re braving stormy weather on your trip to the grocery store or going for a walk around town. Depending on the style, Timberland boots can also be worn on hikes and treks because of their uber-comfortable design and functional, durable soles.

Overall, it’s clear that Timberlands are specifically designed for braving the great outdoors. Whether you need heavy-duty footwear for work or for the snowy streets, there’s a pair for you. With that being said, you may be wondering how exactly to wear your boots. So let’s check out some style tips down below!

How to Wear Timberland Boots

If you’re wondering how to wear your Timberland field boots or any other pair for that matter, there are a few key things to keep in mind. First up, a pair of jeans is always a wardrobe staple, and any pair of these boots go very well with denim. 

Of course, they’re often worn for work, during winter, and on outdoor excursions such as hikes. These truly are tough boots. And when getting dressed, layering your clothes will add a chic yet rugged look to your outfit.

So, try on a few of your coziest sweaters, a nice jacket, and you’ll be good to go. You can also cuff or tuck in your pants for a more casual and comfortable look.

And if the casual look is your thing, try leaving your boots unlaced and pairing them with some cozy joggers for a street-style vibe. On the flip side, super tight laces and chinos will have a dressier, more elevated look. 

Now, like all shoes, before you can think about styling your Timberland boots you’ll need to break them in. Fortunately, we’ve got some tips and tricks to get your new pair feeling comfortable:

  1. Slip on a pair of thick socks and apply bandages to any areas you experience friction
  2. Wear your Timberlands around the house for a 10 minute intervals, gradually building up this time daily, for around a week
  3. Once you start going outside, only wear the boots for a few hours at a time

After that, your boots should be good to go! But, before you break in your boots or even start styling them, you need to pick the right pair of boots for you. Below, we’ll check out the different types of Timberland boots available.

What Type of Timberland Boots Can You Get?

Originating as work boots, The Timberland Company has since expanded their product line to include a variety of designs. Now, they carry boots that meet multiple needs and suit various styles.

From hiking boots to field boots to winter boots, the brand basically has all things boots. They also sell apparel and other types of shoes, but we’re focusing on Timberland boots here.

First up is the classic work boot, which often has a steel toe for protection, a durable leather upper, and a rubber sole, making the shoe both comfortable and functional.

Timberland hiking boots have a more typical ‘hiking boot style’ with a lower top, waterproofing, and multidirectional lugs on the soles for extra traction.

Timberland winter boots come in a variety of designs—from low to high tops—and include different finishes. They also range in style, from casual to more sophisticated varieties, to suit a range of tastes.

The more fashionable boots offered by the brand come with different types of heels, shapes, and a variety of colors for a more aesthetic, stylish look.

Now you might be ready to rock your Timberlands. But, if you need help styling your boots with pieces you already have in your closet, check out these outfit ideas. We’ll take a look at some Timberland boots women’s styles and Timberland boots men’s styles down below. 

5 Outfit Ideas with Timberland Boots for Women

Timberland boots women can wear come in a variety of styles. Whether you’re wearing them with your stylish ensemble, casual attire, or to work, there’s a pair of Timbs for you. 

Chic and Casual

As Gigi Hadid proves, Timberland boots can in fact be chic and casual. Paired with a trench coat in a matching beige color and a fitted knit sweater, this outfit makes the classic shade of these boots stand out. 

With a basic pair of skinny jeans to break up the monochrome look, the boots pop against the blue pants. This creates a seamless and cohesive look, while the mini sunglasses add a trendy touch.


Hailey Bieber also made her mark with a pair of Timbs, opting for something that’s still casual, but has a sophisticated and simple vibe. With a sleek, black fitted mock-neck top and distressed boyfriend pants in bright white, this minimalist look makes the warm shade of these boots pop.

Cozy and Comfy ft. Timberlands

There’s nothing quite like wearing an oversized sweater as the sun goes down, and you really can’t beat warm tones in the cooler weather. There’s just something about a cheery, rosy pink sweater that provides a little relief as we await a world of pale white snow and cool blue skies. 

With comfy black leggings and a chunky pair of Timberlands on your feet, you’ll be able to revel in the last few days of summer while still keeping nice and toasty.

Fall Ready

A green bomber jacket never looked as good as it did paired with your classic Timberland boots. Wear your fave chunky knit, an oversized blanket scarf in an earthy shade, and fitted black jeans for a complete fall ensemble. 

The warm shades in this look will create a sweet and simple fall vibe and you’ll also be nice and cozy. And when you’re picking apples or walking through a pumpkin patch, you won’t be stressin’ about your footwear!

To work, Baby!

With a safety hat on your head, your safety goggles in tow, and an oversized flannel and comfy jeans, your Timberlands will look right at home. Of course, any other gear you need to get the job done will complete the look—from a safety vest to protective gloves, etc.

5 Outfit Ideas with Timberland Boots for Men

Timberland boots men can wear are quite versatile. They can be worn with casual, streetwear, and even more stylish, sophisticated outfits. And, of course, they can be worn to work. Check out the very cool outfit ideas below.

Cool and Casual

With a simple tee and straight-leg jeans, Timberlands have never looked better. Of course, the puffer jacket adds a trendy yet classic touch to the look, while the bold shade of the Timberlands pops against the black jeans. And, of course, the leg of the jeans is tucked into the tongue of the boot for a casual yet thoughtful look.

Mixing Patterns 

When putting together your outfit, there are plenty of ways to play with patterns. Turning the classic lumberjack look on its head, opt for unlaced Timbs, a flannel, and juxtapose them with a loose-fitting pair of camouflage cargo pants. 

Topped with a black tee and a matching black snapback cap, this is a bold outfit. Yet, it’s also simultaneously cohesive and mismatched, creating a unique and eye-catching ensemble.


If you’ve got a taste for trendy streetwear clothes, you’ll be happy to hear that a pair of Timberland boots will fit right in with your outfit. This outfit pairs an oversized white tee, which peeks out of an olive green sweatshirt, with some fitted black jeans for a super casual and put-together look.

The unlaced Timbs complete the look, and the leather jacket in hand is a nice touch. It’s also a great way to add layers to the ensemble. 

Earth Tones

Since the classic pair of Timberlands has a deep, mustard yellow coloring, it only makes sense that Earth tones would match these boots. If you prefer a more styled look, try lacing your boots up, and slipping into an oversized pea coat in a khaki color. 

Wear some olive-colored trousers and a fitted knit sweater, and you’ll have a warm and earthy look. Plus, the outfit is sophisticated, stylish, and fall-ready. 

Denim on Denim 

If you’d prefer a look that’s a little more rugged and handsome, denim on denim is definitely a great choice. Wear a black tee for some added depth, unlaced Timberland boots, and a thick denim jacket with rolled-up sleeves for a complete look.

Your bottoms, of course, ought to be denim too (although you can wear different tones and shades of denim). Roll the ankles up to match your jacket and show off the boots, and you’ll be ready for the day.

How to Choose The Best Timberland Boots

So, you’ve viewed some great pics of people rocking Timbs, and you’ve got plenty of outfit and style inspiration. That means now it’s time to pick your pair. 

But before you get shopping, there are a few key details you should consider to find your perfect boots. Of course, it’s always important to opt for a style that’s in line with your personal aesthetic. In other words, if you don’t have a construction job, a work boot is likely not a necessary option.

On top of that, the brand offers multiple different materials and finishes, all of which are waterproof, that may suit specific preferences. From shoes made of suede, or leather, to shiny and matte varieties, there are lots of looks to choose from. 

Of course, all Timberland boots are made with the highest quality in mind. But, each pair has specific features that meet different needs, including the option of steel toes.

So, it’s important to choose boots that work for your lifestyle. That said, not only are there a variety of choices, there are also a variety of prices, so you can find a pair of Timberland boots that fit your budget. 

With all that in mind, no matter which shoe you choose, it’s important to check out the brand’s size chart and customer reviews to help determine which size is right for you.

Some shoppers state that the brand is notoriously a half size too big, but every shoe is different, so you may want to test them out in-store first (or keep the tags attached).

Fashion Tips to Avoid With Timberland Boots

If you’re interested in purchasing a pair of Timberland work boots, you’ve come to the right place. And if you’re also on the hunt for some tips when it comes to fashion faux pas, look no further. Below, we’ll share some fashion no-nos when it comes to styling your new pair of Timbs.

The first thing to remember when styling your Timberland boots is that they’re not dress shoes. Sure, they can be dressed up with a pair of chinos and a nice top, but they should never be worn with a suit—no ifs, ands, or buts, sorry. 

Another important thing to note is that wider leg pants can look pretty awkward with these oversized boots. Like we’ve mentioned, Timberlands usually look better with a tapered or skinny pair of pants. 

Timbs also don’t really pair very well with shorts. Maybe it’s because they’re traditionally a winter or work boot, but there’s just something kind of freaky about a bare leg against a pair of Timberlands.

How To Take Care Of Timberland Boots

If you’ve got your eyes on a new pair of Timberland boots, chances are you want to keep them looking like new. Below, we’ll share some tips and tricks for keeping your boots feeling and looking fresh. 

First up, of course, it’s important to apply a waterproof protective coating to keep your shoes spick and span. When it comes to cleaning, here’s what you should do step by step:

  1. Remove the laces
  2. Brush away any loose dirt with a bristle brush
  3. Wipe the boots with a soft, damp cloth
  4. Apply boot or leather shoe cleaner
  5. Wash the soles with a toothbrush and soapy water
  6. Rinse with water
  7. Dry the boots with a soft cloth
  8. Buff the boots with a boot brush
  9. Seal them with waterproofing spray

Best Places to Buy Timberland Boots

If our tips for wearing Timberland boots have got you hankering for a new pair, you’ll be happy to hear that there are plenty of places to shop for them. Here’s where you can check them out:

  • Timberland outlet stores and in-person locations
  • Sport Chek
  • Foot Locker
  • SoftMoc
  • Amazon
  • Walmart
  • Nordstrom

Final Thoughts

From cool and casual to bold and well dressed, there are plenty of ways to wear your Timberlands. And with so many pairs to choose from, it’s easy to find something that suits your needs and personal aesthetic. 

Plus, they’re made from super high quality, durable materials, and they’re also very easy to clean—which means you’ll likely have your pair for a long, long time. Now that you know everything there is to know about Timberland boots, we hope that you’ve found a little inspo to style the perfect pair for you. 

Got any other fashion questions on your mind? Check out some of our articles:

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