How to Wear Timberland Boots Outside the Woods (a Cozy Guide)

How to wear timberland boots
Photo: Tom Sodoge / Unsplash

Have you ever tried styling Timberland boots? These functional boots made their way into the fashion world a few years ago, and stylists love them. While some wearers use these sturdy boots for functional purposes, they’re a symbol of street style too.

Perhaps you’ve noticed these popular shoes and want to try them yourself but aren’t sure what to wear them with. If this sounds familiar, keep reading! We’ve put together a comprehensive guide on how to wear timberland boots so you can enjoy this trend without looking like a hot mess.

What Are Timberland Boots?

Before we jump into the best styling tips, we’ll quickly give these iconic boots an introduction. 

Timberlands were established in 1973, making these shoes nearly 50 years old! The original Timberland boots were waterproof and durable, perfect for any outdoor work or activity. The creators didn’t know the humble work boots were set to be fashionable, as they were initially designed for function.

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The waterproof feature of the Timberland boots set the industry standard for water-resistant footwear, and the “yellow” tone of the boots identified the brand. These features still stand strong today, and that’s why many invest in these durable shoes.

How to Style Different Colors of Timberland Boots

While Timberland boots are known for their impressive and unique yellow/beige hue, you can find other color options. Here are some key ways to style the colors:

Traditional Beige/Yellow Boots

If you want to stay with the well-known beige/yellow colorway, you should wear minimal color in your outfit so that the boots stand out.

When you rock Timberlands, you should let their bright color stand out. To achieve this look, wear an all-black or monochrome outfit, and allow your footwear to be the only contrasting color. 

Lilac/Purple Boots

Another popular color for these shoes is the light purple (or lilac) design. This alternative color is soft on the eye and gives a more feminine style.

Though this style works well with many colors, try pairing it with other pastel clothes for a cohesive color palette. If you can’t find any other lilac clothes, try adding baby blue or pastel pink instead.

White Boots

White is possibly the second most popular color of these boots.

If you don’t want to wear the standard beige color but also don’t want a bright or vivid shade, white is a great neutral color option.

These boots work well with most casual outfits, including denim, shorts, and tailored pants, so you have many flexible styling options. Just make sure to keep them clean!

Dark Green Boots

Dark green timberland boots

Timberland boots are popular in all seasons, but they work best in autumn and winter.

Try wearing green boots if you want to keep an autumnal color palette. These go with any dark colors and are more distinctive than most winter shoe options.  

How to Style Different Types of Timberland Boots

Though the most popular style of these shoes is the ankle-length boot, you can find different silhouettes too. Here are our top tips for styling these different boot types. 

Standard Boots


We can’t miss the standard ankle boot length! This is the most common shoe style from this brand, and it’s also the most versatile.

These boots give the wearer a boost with a flat yet chunky sole. It works for street style or elevated casual outfits. We recommend wearing these shoes with denim or flared pants to give your standard style a unique shoe.

Calf Boots


A less common style of Timberlands is the calf boot type.

This style laces to high your calf, making it a flattering option for those who want to accentuate their figure. This shoe works well with skirts or shorts, but it can also sit well over leggings or pants.

Wear this with a cozy scarf and a matching knitwear piece for a casual style. 

Heeled Timberlands 

Our favorite style is the high-heeled type. This takes the standard ankle-length silhouette and adds a dramatic heel. This is perfect if you want to combine the urban feel with evening drama. 

Combine your high heel with a bodycon mini or a faux-leather pant and bodysuit for the best results. 

How to Dress Up Timberland Boots

It’s true that most of the best Timberland outfit styles include casual wear, but you can dress these boots up too. Here are some top tips for dressing up the traditional ankle boot types.

  • Combine the boots with different materials. For example, swap out your casual denim pants for faux-leather pants instead. It makes the outfit more suited to evening events. 
  • Wear the boots with a high-waisted skirt (or shorts) and a crop top. High Waisted styles flatter all body types, making us look taller and slimmer. These boots will give you an extra boost to improve the look of your figure for any evening affairs. 
  • Add a matching jacket. You can find jackets that match the beige/yellow tone of the boots. Combining a bomber jacket or blazer that color matches the boots automatically makes your outfit look more dressy. 
  • Take your best purse. While it can be tempting to leave your best purse at home to preserve it, sometimes adding a luxe accessory can make your outfit go from great to super.
  • Swap your denim jacket for a tailored look. If you’re used to wearing your Timberlands with casualwear, try swapping one garment for a more formal version. It could be your jacket, or even your t-shirt for a blouse too.
  • Pair the boots with cargo pants for a relaxed and super-comfy outfit.

Timberland Boots Outfit Ideas

If you still aren’t feeling inspired, here are some quick outfit ideas to help you curate your new Timberland wardrobe options. 

Timberland Boots With Jeans

Jeans are an easy styling tool. We all own jeans, and they work with pretty much any shoe, so it’s good to know how to pair them with your boots.

When it comes to these shoes, try pairing them with dark denim to allow the boots to stand out more. Add a feminine crop top to finish off the street style look too. 

Timberland Boots With Blazer

A blazer might not be your first thought when it comes to styling these shoes, but it’s a very effective combination. Urban street style isn’t everyone’s niche, so adding a blazer or tailored coat can take the outfit from too laidback to city-ready in seconds. 

Timberlands With Shorts

Timberlands can be worn in summer!

Despite looking like winter shoes, these thick boots make great hiking and general summer footwear. Pair them with cropped denim shorts and a cropped slogan shirt for a relaxed look. It’s also popular to pair these boots with longer or statement socks if you feel daring!

Timberland Boots Size Guide

When you’re investing in a new pair of shoes, you want to make sure the sizing is just right. If you’re buying Timberlands, ignore the common myths stating “go a size up for an extra room.” Timberland shoes do run true to size. Make sure you purchase a pair in your standard shoe size to ensure the best fit. 

If you aren’t sure what your shoe size is or don’t want to make a mistake, it’s best to buy these shoes from an in-store retailer. This way, you can get your feet measured by a professional in person, and you’ll also have the chance to try the boots on before purchase.

How to Lace Your Timbs Like a Pro

Photo: Kal Visuals / Unsplash

Though these shoes often come pre-laced, there are various ways to lace Timbs. The most common patterns include:

  • Standard lacing
  • Cross-cross lacing
  • Army Style lacing
  • Loose lacing

Standard lacing is threading the lace through the eyelets from the inside of the shoe. Once this is complete, keep threading the laces from side to side for a traditional laced boot style. Finish this with a bow at the top of the shoe.

If you want an alternative or decorative lacing style, we recommend army-style laces. This keeps the shoe well laced and looks more intricate than standard shoe lacing. To do this style, thread the laces through the eyelets above the previous lace and don’t criss-cross. You only cross the laces over when you go up an eyelet, keeping the upper side of the shoe free from criss-cross laces.


Want to learn more about this iconic footwear? Here are some FAQs.

Are Timberlands Waterproof?

All footwear from this brand is waterproof. The main body of these shoes is crafted from genuine leather produced and tanned to be water-resistant. While leather can never be 100% waterproof, these shoes are also coated by a water-resistant spray to ensure your feet stay dry. 

Can Timberland Boots Be Considered Smart Casual?

Though these shoes started life as workwear footwear, they’ve transcended this functional sector and are now considered smart casual shoes. The brand is well-known, and the products are always crafted to look smart, so as long as you pair the boot with a shirt and tailored pants, you can wear them to smart-casual events.

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