The Timberland six-inch work boot has come a long way over the past fifty years.

Released in 1973 (when the brand was still known as the Abington Shoe Co.), the hardwearing, waterproof “Timberland” had a largely practical purpose: to protect the tootsies of New England labourers from harsh weather and construction site mishaps, and they did a fine job of it. The shoe became so popular, in fact, that five years later the company renamed itself after the best Timberland boots for men.

But two decades on from release, something unexpected happened – something that left the blue-collar brand baffled. Over in New York, the boot had found its way onto the feet of the biggest names in hip-hop, from Biggie Smalls to Nas to Mobb Deep to Tupac. The yellow nubuck design became so ubiquitous in the scene that they were regularly referenced in lyrics, too. (Biggie packed some existential style advice into ‘Suicidal Thoughts’, the last track on his debut album: "Doesn't make sense goin' to heaven with the goodie goodies / Dressed in white, I like black Timbs and black hoodies"). Timberland owes much of its success to that period, and the legacy it left.

Timberland 6 Inch Boot

Timberland 6 Inch Boot

Timberland 6 Inch Boot

£190 at timberland.co.uk
Credit: Timberland

The shoes still hold a special place in hip-hop culture. Kanye West, ASAP Rocky and Drake have been regular wearers (the latter even receiving his own OVO-branded Timberland silhouettes a few years ago). The label has also collaborated with a number of streetwear brands and designers, most notably the late Virgil Abloh, who released Off-White’s first take on the iconic work boot back in 2018. Recently, cult New York label Alife released a 7.5-inch version.

Timberland Alife x Timberland® 7.5 Inch Boot

Alife x Timberland® 7.5 Inch Boot

Timberland Alife x Timberland® 7.5 Inch Boot

Credit: Timberland

The brand has also upped its eco-credentials over the past few years, all with an aim of achieving 100 per cent sustainability by the end of 2030. They've even introduced a new 'Timberloop' system, whereby customers send their old boots to the company's manufacturing plant (free of charge) and get 10 per cent off their next purchase. Not a massive discount, granted, but you have to factor in that it'll make you feel like Greta Thunberg for a few days afterwards too.

Needless to say, there are plenty of different colourways and variations available. Check out our picks of the best Timberland boots for men below:

timberland
6 Inch Boot in Black

SHOP

£180, timberland.co.uk

Timberland
timberland
6 Inch Boot in Orange

SHOP

£180, timberland.co.uk

Timberland
timberland
6 Inch Boot in Light Brown

SHOP

£190, timberland.co.uk

Timberland
timberland
Warm-lined 6 Inch Boot in Yellow

SHOP

£147, timberland.co.uk

Timberland
timberland
Warm-lined 6 Inch Boot in Black

SHOP

£147, timberland.co.uk

Timberland
timberland
6 Inch Boot in Yellow

SHOP

£154, timberland.co.uk

Timberland

And as for the rest of your outfit, have a gander at our weekly edit of the coolest clothes for men here.