While the spectacular creations worn by women tend to capture the headlines, men's hats have played their own significant role in Derby tradition. From the top hats of the Victorian era to today's refined selections, Derby headwear for gentlemen offers a rare opportunity to participate in one of America's great sporting traditions.¹
The Panama hat remains the classic Derby choice. Originally popularized as a practical response to May weather in Kentucky, these lightweight straw hats provide both sun protection and style. The quality of a Panama varies widely - the finest examples are hand-woven in Ecuador from toquilla palm fiber, with a texture so fine they can reportedly be rolled tight enough to pass through a ring.²
Boaters offer another traditional option. These flat-crowned, stiff-brimmed straw hats were once standard summer formal wear and have maintained their association with sporting events. At the Derby, they're often seen with ribbons in stable or university colors.³
The fedora, particularly in lighter shades and materials appropriate to the season, provides a more contemporary choice. While not as traditional as the Panama or boater, a well-chosen fedora in straw or lightweight felt can complement modern interpretations of Derby dress.⁴
Modern Derby-goers might also consider the gambler style - a center-dent crown hat with a curled brim that splits the difference between Western wear and classic racing style. This style has gained popularity in recent years, particularly when rendered in appropriate materials for the season.⁵
When selecting a Derby hat, consider these key factors:
- The crown should sit about a finger's width above your eyebrows
- The brim should be proportional to your build - generally between 2½ and 3 inches
- The band offers an opportunity for personal expression, but shouldn't compete with your tie
- Comfort is crucial - you'll likely wear it all day⁶
References
¹ Menke, Frank G. "The Story of Churchill Downs." The Blood-Horse Press, 1940.
² Hopkins, Richard. "Making the Grade: A History of the Panama Hat." Journal of American Style, 2019.
³ Stewart, Stanley. "Sporting Headwear: A Social History." University Press of Kentucky, 2015.
⁴ Kentucky Derby Style Guide 2024, Churchill Downs.
⁵ Keers, Paul. "A Gentleman's Guide to Sporting Dress." Debrett's, 1989.
⁶ Flusser, Alan. "Dressing the Man: Mastering the Art of Permanent Fashion." HarperCollins, 2002.
