The cycling cap, a beloved accessory in cycling culture, boasts a fascinating history intertwined with the sport's evolution. Dating back to the late 19th century, cycling caps, also known as "casquettes" or "cycling hats," emerged as essential gear for cyclists, offering both protection and style. Crafted initially from wool, these caps featured a distinct design with a short brim and soft crown, providing ventilation and shielding riders from the elements. Over time, cycling caps evolved with modern materials like moisture-wicking synthetics and varying brim lengths for enhanced sun protection. Today, these caps remain iconic within the cycling community, often adorned with team logos and sponsor branding, serving as both functional gear and fashion statement. Whether for competitive racing or leisurely rides, the cycling cap continues to hold a special place in cycling culture, symbolizing tradition and identity.

But who wore it best?

This list, although numbered, is in no particular order. Its almost impossible to answer and our thoughts on this are constantly changing. However here is our current top 6.

1. Sean Kelly

Adding Sean Kelly is more of a formality than anything else. A list of this nature cant be compiled without an honorable mention of the Irish man.

Sean Kelly Cycling Cap

Photo: Getty

2. Wesley Snipes in White Men Cant Jump

With his undeniable charisma and swagger, Snipes' depiction of Sidney Deane, complete with the Colnago cycling cap, remains an enduring symbol of '90s pop culture and streetwise style.

Wesley Snipes cycling cap

Photo: 20th Century Studios

3. Djamoulitdin Abdujaparov

"Tashkent Terror" - The most flamboyant sprinter of the 80's and ever. Always donning his cap at a jaunty angle, often askew and flapping in the wind, it seemed to mirror his relentless pursuit of victory. His unruly mane of hair would sometimes peek out from underneath, adding to his wild and untamed appearance as he tore through the peloton.

Photo: Getty

4. This guy

High fashions streamlined silhouettes, vibrant colors, and technical fabrics echo cycling apparel. Accessories like cycling caps and musettes are reimagined luxuriously. This fusion creates a captivating blend of contemporary fashion and sport. Here we have a some pieces from a Moschino catwalk show. Moschino have always drawn inspiration from cycling.

Moschino cycling cap

Photo: Vittorio Zunino Celotto/Getty Images

5. Eddy Merckx

Eddy Merckx, often hailed as the greatest cyclist of all time, possessed a style on the bike that was both relentless and elegant. His riding was characterized by an insatiable hunger for victory and an unmatched versatility across all terrains. Merckx's style was marked by his aggressive attacks, often pushing the limits of his competitors with relentless pace-setting and daring breakaways. Eddy knew how to rock the cycling cap correctly.

Eddy Merckx cycling cap

6. Primoz Roglic

Finally a favourite of The General Classifications's, the doer of no wrongs: Primoz Roglic. Pictured here as cool as a cucumber. 

Primoz Roglic Cycling cap

Photo: Massimo Paolone

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February 23, 2024