How to Wear Timberland Boots

by Jamie Wilson

Reviewed & updated: October 19, 2022 by Jamie Wilson BA

The humble Timberland boot has been falling in and out of style for as long as we can remember. While, understandably, it has its moments where it can better suit the prevailing style, but when worn correctly, it can work regardless of its popularity. To show you exactly how it’s done we’ve put together some essential looks and the accompanying pieces to let you rock your boots with style.

Timberland Boots: Outfit Inspiration

Timberlands are everywhere. So many people own a pair of Timberlands which make great shoes for multiple reasons. These boots can, however, be tricky to style. That’s why we have put together this quick guide on how to wear different Timberlands with different looks. With these following looks, you should be able to style your Timberlands with ease.

The All-black Outfit

For a style more suited to streetwear, try out an all-black ensemble with some slim fit ripped (or unripped) jeans. The slim cut jeans lend themselves well to the chunkier fit of the boots. Wear this with a black jacket to enhance the all-black look. To make it look the best it can, try to go for plain black clothing as patterns might disrupt the vibe you’re going for. You could either wear a street-style jacket such as one from The North Face or go for a smarter one (depending on the style you want to go for). Top off the look with a plain black T-shirt underneath your jacket and of course, a pair of classic Timberland all-black boots. Easy!

Adventure Cupsole Timberland Boots

Timberland boots are also spot on for the current workwear trend. They’re totally in line with the durability and rugged aesthetic. Without pushing the boat out too far, the outfit below shows how versatile their styles are. You might think of Timberland and automatically assume a pair of 6″ Premium boots are your only option – this is not the case. Timberland caters to most styles and these Adventure 2.0 Cupsole Chk Tan boots are some of our favourites. They make a great alternative for those who despise wearing chunky boot son their feet/ankles. This look can be teamed with a pair of raw denim roll-up jeans and a simple, plain white T-shirt for a relaxed vibe that can also pass as being dressed smartly. To go even more smart, layer a shirt over the white T-shirt, buttoned or unbuttoned.

Stick To Basics

You can never go wrong with staple pieces, no matter what the look is. Try pairing the chunkier silhouette of a pair of Timberland boots with some plain black jeans. We’d go for a slim leg fit for this to keep it smart-casual. You can then put anything up top, from a white Oxford shirt to a simple white T-shirt. Why not layer over a plain sweater for a failsafe combination that will be ideal to match with your jeans. If it’s a chillier day, layer up again with a parka jacket for a snug and rainproof finish.

Dress Them Up

Who said a pair of Timberland boots can’t be dressed up? With a black pair of boots it’s certainly possible, as long as you get the rest of the outfit right too. Start with a pair of trousers – a slim-fit pair of chinos is a great place to start as they give off a smarter vibe than jeans do. You could equally go for a pair of suit trousers, as long as they are loose at the ankle. Next, you need to make sure your ankle is on display (with socks). You can achieve this by either buying a cropped pair of chinos/trousers, by going to the tailor and getting them taken up or by rolling them up (this will only work for chinos). Don’t worry, there are plenty of looks where cropped trousers will be your go-to, so it won’t be a pair wasted by any means.

Next up, the top half. To play it safe, opt for a roll neck top or jumper and partner it with a smart black jacket. A peacoat or an overcoat is your best bet.

How to Wear Timberland Boots

  • Timberland boots are very versatile so you can wear them with a lot of outfits. Don’t be afraid to play around with different looks in front of your mirror until you find one that suits you.
  • Stick to basics. If you want a failsafe look, stick to wearing some dark blue or black slim-fit jeans and a plain white T-shirt with your Timberland boots.
  • Pick your pair. Timberland have many different styles of boot, so you are in no way limited to which ones you have to wear.
  • You can dress them up as long as you know the look you are going for. Avoid jeans and bright colours when dressing up your Timberlands.

On That Note

Whether you want to channel the ultimate chic street style vibes or you prefer a more subtle look, Timberland boots are so versatile that they’re a trusty option for most outfits you’ll want to put together. You can dress them up or down, depending on the occasion. Dressing the Timberland boots down is easy – all you need is a pair of jeans and a T-shirt. Dressing them up can be a little more tricky, but stick to one or two colours only, avoid jeans and pair them with a black overcoat and you should be fine. There are plenty of Timberland styles out there, so you are in no way limited to just one type. After reading this guide, there’s no way you’ll run out of ideas on how to style your boots!

Feature image from Pinterest

You may also like