A Guide To Wearing & Styling Timberlands For Men (2024)

Written by Jeff Lack

Originally created in 1973 as an all-weather, outdoor boot for the frigid New Hampshire winters, the original yellow 6” Timberland has become an enduring fashion icon. Worn by tradies and musicians alike, it’s been adopted by everyone and anyone; a symbol of the contemporary ‘Made in America’ aesthetic.

Today, the ‘Yellow Boot’ has far surpassed its outdoor heritage and can be worn in a range of different ways. And whether you’re slipping them on to battle against the snow or they’re your go-to street shoes, there’s an art to wearing them. Here, we explain the best ways to sport this classic and ensure these stompers keep you looking fresh.

Timberlands With Denim

Adored by Yeezy himself, the Yellow Boot and jeans is the simplest look in the books. Slim cut denim and a pair of Timberlands with the tongue flopping out gives you instant street cred, regardless of how you style it.

However, for maximum impact it’s worth giving this look a little more thought. The top of your outfit in particular can change the feel entirely so think about the occasion and curate your look to reflect this. For drinks or going out, look at pairing dark jeans and Timberlands with a button-down shirt. Mr. West makes a strong case for a denim chambray shirt but a white or pale blue Oxford would look equally strong. Alternatively, if you’re chucking this on for a quick trip to the shops or coffee, lean in to these boots’ outdoorsy heritage. Plaid shirts and trucker caps are the name of the game and will give you a ruggedness even if you’re nothing of the sort.

Timberlands With A Bomber Jacket

Timberlands and bombers play in the same fashion heartland: street wear. There’s something inherently cool about both that lends to them being shrugged on without too much thought. When it comes to choosing the type of bomber you pair your boots with though, a level of discernment is key.

Because Timberlands are a relatively bulky shoe, it’s important to balance out your outfit with a bomber that isn’t too puffy. Find a classic nylon or satin version that has slim sleeves and finishes on your waist. This will make your outfit appropriately proportioned. If you go for the classic yellow boot, also think about bomber colours that play well with mustard. Burgundy and khaki lend themselves naturally as a contrast and look great layered over a plain grey tee and dark jeans.

Timberlands With Cargo Pants

Cargo pants have been experiencing a resurgence of late and, whether you like it or not, they’re well and truly back on the high street. Getting away with them without looking like a bad 90s rapper is a challenge though. Particularly for your average punter.

If you are taking the plunge (and pairing them with Timberlands no less), simplicity is key. Unlike the cargos of yore, the contemporary iteration should have fewer pockets and be in earthy shades like brown or black. Opt for a slim fit and pair it with a plain crew neck tee shirt. Whilst this look is street, it shouldn’t feel sloppy. Finish it off with a well-cut denim jacket and you’ll be ready to go.

Timberlands With A Coat

If, like me, you wear Timberlands for their original intended purpose; when it’s bloody freezing; chances are you’ll also be donning a winter coat. Coats, beyond just being practical, are an opportunity to elevate your look and give it additional polish. This is even more the case when it comes to these classic boots.

Having a high-rise side, Timberlands give you permission to experiment with a longer style coat. Explore knee length camel options that look just as good with jeans and a hoodie as they do with a suit. Alternatively, a double-breasted pea coat is an equally stylish method for upping the ante on your Timberlands – pair them with dark chinos, a chunky knitted scarf and a beanie for the consummate winter look.

Timberlands With Sweats

I’m of the Karl Lagerfeld school of thought when it comes to sweatpants; they’re ‘a sign of defeat’ and something would have gone terribly awry if I was wearing them in public. Nevertheless, with increasingly high-tech (and fitted) iterations entering the market, they’ve become semi-acceptable in the public sphere. And runners aside, Timberlands are one of the only acceptable shoe options you can pair them with.

The key to pulling this look off is elevating your sweats with an interesting jumper or bag. Think plain ankle zip track pants worn with your boots and a Kenzo sweater. This balances out the baggy bottom half with something more polished. Finally, if you are going for this most casual of looks, it’s vital that everything is pristine. Not even a pair of Timberlands will save you from a grease stain on your trackies.

Timberlands FAQ

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