Brooklyn rapper Lola Brooke is the new face of Timberland’s latest commemoration of hip-hop’s legacy for its 50th anniversary. Though both were established in 1973, there was once a time when the iconic boot company didn’t want to be associated with the music genre.

Timberland released a purple six-inch “Hip-Hop Royalty Boot” inspired by the original yellow boot featuring Bed-Stuy, Brooklyn newcomer Lola Brooke in the new campaign. The release commemorates Hip-Hop’s 50th Anniversary along with their own since both were introduced to the world in 1973.

Timberland introduced the six-inch yellow boot as a durable work boot for blue-collar workers. The boots were designed to withstand harsh weather and terrain and became a staple of the construction and logging industries.

Timberland’s Rise Of Popularity In Hip-Hop

Hip-Hop made Timberland the billion-dollar company it became today. However, the iconic brand rejected hip-hop in the 1990s when rappers were spotted in their classic boots. 

The brand was concerned that the association with the music genre would damage its reputation as a high-quality work boot. 

“It’s not what we intended. It’s not where we come from,” Timberland’s then-executive vice president and founder’s grandson, Jeffrey Swartz, said in the past. 

In November 1993, Swartz was featured in a New York Times article detailing the brand’s hesitation to embrace hip-hop and distance themselves from consumers they thought were buying their product for the “wrong reasons” or in the name of fashion. Timberland eventually recognized the value of its new audience and began to embrace its association with the hip-hop culture. 

The brand began to feature rappers in its advertising campaigns and even released a line of boots designed specifically for hip-hop.

The popularity of Timberland boots in the hip-hop culture significantly impacted the brand’s identity. The boots have become a symbol of authenticity and toughness and they are often used by rappers as a way to project a certain image. 

For Timberland, the association with hip-hop has helped broaden the brand’s appeal and introduce it to new audiences.

Timberland’s ‘Ode To Hip-Hop’

The brand’s celebration of hip-hop is just the tip of the iceberg as many other pioneers and contributors of the genre have celebrated and paid homage, including “A Love Letter To Hip-Hop” from Black Thought. DJ Premier chimed in by releasing a new album, Hip-Hop 50 Volume 1, through Nas’ Mass Appeal label.  

In addition, Public Enemy’s Chuck D also celebrated 50 years of hip-hop with programming, including “Legends In Concert,” “Hip-Hop International,” and “2K Hip-Hop Legends,” with Vevo.

The new boot honors the pillars of hip-hop – DJ’ing, MC’ing, graffiti, and breakdancing and, of course —  Sedgwick Ave in The Bronx, New York — the birthplace of it all — within the markings and presentation of the shoe as well.

The purple tongues on the boot reference its connection to royalty, including a graffiti mural in the Bronx dedicated to hip-hop’s founder DJ Kool Herc on West 179th St between Cedar and Sedgwick Avenue in the Bronx.

The gold eyelets and collar complete the regal look. The gray soles evoke NYC’s nickname of “Concrete Jungle,” while the Helcor fabrics on the backstay mirror the texture of vinyl records. 

The green labels on the tongue resembling a street sign are imprinted with the words “Sedgwick Avenue” in honor of where the iconic musical genre was created. 

Additional details include hang tags resembling DJ turntables, mic cord-like aglets, Timberland’s tree logo reinterpreted as a graffiti tag across the sides, and the thick serrated sole synonymous with the original yellow boot.

Rappers Who Made Timberland Boots Iconic

In the 1980s, Timberland was not a staple of hip-hop fashion. However, early hip-hop artists, like  Grandmaster Flash, the Furious Five, and Run-DMC, were known for their love of Adidas sneakers and tracksuits. 

These styles became the early fashion staples of hip-hop culture. It wasn’t until the 1990s Timberland boots symbolized authenticity and toughness in hip-hop culture.

Wu-Tang Clan

The legendary hip-hop group Wu-Tang Clan frequently wore Timberland boots, with member Ghostface Killah famously rapping about them in the song “Daytona 500.”


The Queensbridge rapper was also known for wearing Timberland boots, and also rapped about them in the song “Nas Is Like.”


The late rapper was another artist who frequently donned Timberland boots. He even had a song titled “Timberland” on his album The Great Depression.


The rap mogul and entrepreneur has also been known to rock a pair of Timberlands. In his music video for the song “Can I Live,” he can be seen wearing a pair of the classic tan boots.


Although the California rhymer was known for his signature bandanas and baggy clothing, Tupac also sported a pair of Timberland boots.

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