Music and shoes have more than a little shared history, they’re practically sole mates. The two industries have been inextricably laced together for decades, each channeling the mood of an era in their own respective ways. Consistently remaining icons of style, we look at how they’ve always been a step ahead of everyone else.

Vybz Kartel
Image credit Google ©

Clarks Chukka Boots

Jamaica’s long-standing affinity with Clarks is evidenced by the wide range of Jamaican artists who choose to promote the brand. Vybz Kartel is one of dancehall’s most famous success stories and, accredited as one of the genre’s most prolific and skilled lyricists, he’s also a strong advocate of Clarks. In 2012, he even dedicated an entire song to the British shoemaker.

Like the brogue, the loafer and the Chelsea boot, the Chukka boot is a perennial British classic that hails, as many of our tailoring does, from the military. These shoes are ideal for those who want to bridge the gap between formal and informal. They are the smart-casual lover’s dream—for adults with a sense of style, this is a shoe based on something enduring rather than something faddy.

After the second world war, Chukkas went from being an imperial sports shoe to a casual wardrobe staple. Their most famous incarnation—the Chukka desert boot—gained popularity among Jamaican rudeboys and has remained big on the island ever since. All desert boots are Chukkas, but not all Chukkas are desert boots. Therefore, the desert boot is a subset of the Chukka.