Pencil Thin Mustache Contest

Do you have the perfect pencil-thin mustache—or something a little more… Bubba?

Join Just a Few Friends, the legendary Chart Room, and Beards and Brews for the 3rd Annual Mustache Contest—a lighthearted tribute to one of the most iconic looks (and songs) in island lore.

Whether your ‘stache is real, ridiculous, or completely made up, there’s a category for you—and plenty of laughs along the way.

🏆 Categories

— Best Look-Alike

— Best Pencil-Thin Mustache

— Best Creative Mustache

🎖️ Category winners advance to People’s Choice Best of Show, where one grand champion will take home an unforgettable prize package—including Key West Express tickets, a two-night stay at the Pier House, dinner at One Duval, a limited-edition bottle of First Legal Agave Spirits, and ultimate bragging rights.

📍 Set in the iconic Chart Room—where the stories are real and the history runs deep—this is one of those only-in-Key-West moments you don’t want to miss.

Registration: noon to 12:30 pm

Contest: 12:30 pm to 1:30 pm

A Bit About the ‘Stache

The pencil mustache rose to popularity in the 1930s and ’40s, worn by Hollywood icons like Clark Gable and Errol Flynn as a symbol of suave style. It found new life in 1974 with “Pencil Thin Mustache,” a nostalgic, tongue-in-cheek tribute to a bygone era—celebrating the characters, quirks, and cultural moments that helped define a generation. That same spirit of fun and personality is what this contest is all about.