12 Ways to Style Timberland Boots, the Ultimate Weather-Proof Shoes

It’s not every day that you’re able to get a leather shoe that’s timeless and crafted with leather for under $200. But as the 50th anniversary of the iconic Timberland boot came and went, it got me thinking about how the simple yellow lace-ups have managed to stick around for five decades and then some. 

Originally released in 1973, the iconic style was introduced as an answer to inclement weather conditions. The boot quickly became popular among people working outdoors seeking a water-resistant and more comfortable solution. By the late ’80s and early ’90s, the shoe was already being embraced by people all over the world, including in Italy, the UK, and Japan. It was still considered practical, but it was also beloved for the Western fashion symbol that it represented. Hip-hop artists, including Biggie Smalls, Tupac, and Nas, were key in catapulting Timberland boots into an iconic accessory in pop culture.

To this day, the boot is regularly worn by influential fashion figures along with celebrities like J.Lo, Rihanna, and Emily Ratajkowski. Designer brands like Jimmy Choo, Supreme, and most recently, Louis Vuitton have all collaborated with the brand, proving that the cult classic style probably won’t be going anywhere. So jump on board with these 12 ways to style the timeless and utilitarian Timberland boots below.

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With A Tailored Coat

As we step into boot season, Timberlands are a foolproof way to inject effortless style into any outfit. But if you want to be extra put together like style icon Veronika Heilbrunner, pair them with a menswear-inspired look. A tailored coat and button-down will be key to nailing this look. Add a tie and your favorite Louis Vuitton handbag if you want to feel super chic.

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With A Maxi Skirt

If you thought that Timberlands could only be worn with pants, think again. Their yellow tone goes perfectly with the season’s most popular shades like brown and burgundy. A sleek maxi skirt in a deep chocolate hue will add major chicness to balance out the rugged boot. Add a bunch of layers for maximum coziness. 

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With A Barn Jacket

Ever since Prada sent barn jackets down their spring 2024 runway, it seems like the workwear trend is everywhere. Luckily, the originator of the barn jacket or the “chore coat,” Carharrt has so many options available. The barn jacket pairs so well with a pair of Timberland boots, not only because of their matching tones but also because of their inherent workwear nature. Style with baggy jeans and a cropped top and you’ll be good to go. 

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With A Tweed Dress

There’s something unexpected, yet harmonious about wearing a pastel tweed dress with a pair of socks and Timberlands. It’s the non-obvious footwear choice for this kind of outfit but I think that’s precisely what makes it work. Add a colorful knit and your favorite crossbody to style out the full look. 

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With A Matching Trench

You can’t deny that Timberlands are a fantastic, neutral color for fall. In this case, you should probably pair them with a matching leather trench coat. Wear an easy all-black look underneath to let your boots and coat do all the talking. 

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With A Printed Jacket

Sometimes all it takes to pull off Timberlands is your favorite pair of slouchy jeans and a cool printed jacket. Christine Würfel-Stauss took the streets of New York Fashion Week wearing a silver and blue Louis Vuitton evening jacket from the brand’s 2018 collection. She accessorized the yellow boot look with a black mini Hermès Kelly and sunglasses. 

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With Lots Of Layers

One of the best features of Timberlands (dating back to their inception) is that they are perfect for harsher conditions. So when the temps drop down to frigid, you can bet that your booties will keep you dry and comfortable no matter the forecast. Pair with lots of layers like a cozy hat, shearling coat, and even a maxi dress over a pair of joggers for optimal warmth. 

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With a Blazer and Hoodie

An oversized blazer styled over a hoodie is one of my personal favorite outfit combinations. You can wear the formula with any kind of denim style and shoes, really. So don’t forget about your Timberlands the next time you put on your go-to, easy look.

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With a Denim Tuxedo

Ask any fashion editor and they’ll tell you that denim on denim works with almost any trend—and this time is no different. Take a page out of Stephanie Sanchez’s book by pairing your Canadian tux with a crisp white button-down, a fun printed tie, and duh, your Timberland boots.

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With A Textured Coat

Looking for a way to shake things up? My advice is to add a bit of texture to your look with a plaid wool jacket, for example. Bonus points if you find one in a standout bright color like mustard yellow. Oh, and a geometric handbag will add even more dimension—trust me on this. 

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With a Cropped Bomber

One thing about Timberland is they’re going to come out with different versions of their classic boot. Whether it’s in the color, the heel height, or the shape, there is no shortage of options over at Timberland. Case in point: these mid-heel lace-up Timberland boots were seen at Copenhagen Fashion Week. With just a little more height, you can really lean into your feminine side with a denim skirt and a cropped bomber jacket. 

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With a Tracksuit

On any given work-from-home day, you can find me rocking a pair of Adidas track pants. And good news for me is that they lend themselves so well with a pair of Timberlands. Next time I step out for my morning coffee, it’ll be in this sporty but comfy tracksuit and boot outfit.