We love a comeback. And 2023 has played host to so many of them in fashion. Highlights include: Mowalola coming home from Paris to show at February London Fashion Week; Skepta shutting down September London Fashion Week with the relaunch of his marque Mains; the grand return of cult label ASAI, brainchild of Woolwich-raised designer A Sai Ta.

All stellar moments in their own right, but what's most fascinating is that, location aside, the throughline of these comebacks is another comeback—one of the American fashion kind. With a leg up from London, Timberland's boots have been stomping back into our lives (and onto our social feeds) in the very year it's celebrating its 50th anniversary.

Not that it ever really went away. The nubuck leather stomper—invented by the brand's Ukrainian-born founder, Nathan Swartz, with the help of his son, Sidney, in Boston, Massachusetts, in 1973—is the mainstay of many a shoe rack. In its early years, the Timberland boot was espoused by the very people that it was designed for: the blue-collar workers of New England and beyond. Said labourers appreciated that the design was resilient, protective, warm, and, thanks to Swartz’s employment of injection-moulding technology, waterproof. But it wasn’t long until the versatile footwear option transcended its target market.


In Milan in the Eighties, the tread was pivotal to the Paninaro. (Paninaro: a social phenomenon that saw the young bourgeois of the Italian metropolis forming cliques in and around sandwich shops and fast-food restaurants, yielding to Americanisation in response to the social unrest of the city in the seventies.) Alongside a Moncler puffer, a pair of Timberlands was a requisite part of their Italian-American uniform.

And in the early nineties, British ravers and Japanese Yankophiles embraced the traditionally-wheat-coloured kick. But, in retrospect, such events were mere build up to the brand's defining moment: the NYC hip-hop scene's adoption of "The Original Yellow Boot" in the mid-nineties.


“Seemingly overnight, Timberland and companies like Carhartt Inc and North Face, which have made their reputations on manufacturing authentic outdoor and work apparel, have, in the parlance of the street, become ‘dope’ and ‘phat’,” wrote Michel Marriott for The New York Times in 1993.

It is said that the city's rappers were put onto 'Timbs' by the hustlers of Harlem who would cop the formidable shoes from the brand's Madison Avenue flagship and wear them whilst doing business throughout the night. Ostensibly, they affiliated the boot with the hood that they sought to symbolise.

Timberland boots have been indivisible with hip-hop—and, by extension, streetwear—ever since. To celebrate the Timbnaissance—as well as the brand's 50th anniversary documentary titled This is Not a Boot: The Story of an Icon, which dropped this week—we've collated the top moments when Timberland left a footprint on culture through the agency of the hip-hop community.

Tupac At The 7th Annual Soul Train Music Awards (1993)


In 1993, Tupac Shakur presented the Timbs 'fit blueprint: baggy denim + streets-approved accessories + The Original Yellow Boot.

Raekwon (Wu-Tang Clan) In New York City (1993)


Raekwon and the rest of the Wu-Tang Clan have been sporting Timberland boots ever since the collective was formed in the early nineties.

The Notorious B.I.G At The KMEL Summer Jam (1995)


The man who once rapped, “Timbs for my hooligans in Brooklyn” performed in a chocolate brown pair of Timberlands, in addition to his other style essential, Versace shades, at ‘95's KMEL Summer Jam.

Busta Rhymes At The Source Hip-Hop Music Awards (2000)


Stylist June Ambrose recently revealed to Footwear News that after Hype Williams' zeitgeisty music video for Busta Rhymes' 1997 hit 'Put Your Hands Where My Eyes Could See', the rapper “would not go on stage without the matching Timberlands to every customised look”.

“It was disruptive and sexy and provocative and very hip-hop.”

Diddy In New York City (2003)


A decade after Timberlands began to pop-up on the feet of hip-hop's greatest, Sean Combs rocked some wheat-hued Timbs with a get-up typical of the rap set at the time.

Cam'ron In The Dipset Anthem Music Video (2003)

Pink has always been Cam'ron's trademark colour. 14 years prior to the release of his song with blackbear, 'bright pink tims', the Harlem-born rapper wore a pair of pink bandana-print Timberland boots in the "Dipset Anthem" music video.

LeBron James At The MTV Video Music Awards (2003)


Hip-hop fanatic LeBron James paid homage to the music genre at the 2003 VMAs via an archetypal Timberland boot.

Tupac hologram At Coachella (2012)


In 2012, Tupac's estate decided a pair of Timberlands is elemental to the late rapper's quintessential attire, as evidenced by the shoe's presence in his posthumous hologram.

Kanye West In Los Angeles (2012)


Watch the Throne-era Ye captured in a seminal ensemble that is largely responsible for Timberland's ubiquity during the early tens.

Drake In "The Hotline Bling" Music Video (2016)

Drizzy kept the legacy afloat in the mid tens by teaming a pair of six-inch Timberlands with a turtle neck and joggers in Director X's indelible music video for 'Hotline Bling'.

Pharrell Williams At The BET American Black Film Festival (2017)


Pharrell Williams—founder of Timberlands' regular collaborator, Billionaire Boys Club—put a bohemian twist on a Timbs 'fit in 2017, serving the world with a reminder of the boot's versatility.

Rihanna In New York City (2023)


Bellwether Rihanna ushered The Timberland Boot into yet another decade earlier this year, updating a nostalgic vest/baggy jeans/Timbs combo by pairing it with modish accessories.

Beats Studio Pro, Presented By A$AP Rocky Advert (2023)

Rihanna's other half, A$AP Rocky, verified the 2023 Timberland resurgence in his ad for Beats by Dr Dre's Studio Pro headphones. In it, the trendsetter is clad in some Timbs whilst running across a NYC neighbourhood to grab some diapers.

Originally published on Esquire US