Pencil Thin Mustache Contest

Do you have the perfect pencil-thin mustache—or is yours more on the bushy side, Bubba? Just a Few Friends, The Chart Room at the Pier House, and Beards and Brews invite you to showcase your facial hair flair in our Second Annual Mustache Contest for a shot at epic bragging rights and fantastic prizes. This spirited event pays homage to the iconic song “Pencil Thin Mustache” and the unforgettable facial hair that often accompanied a certain beloved island troubadour. Whether your look is legendary, laughable, or lovingly fake, we've got a category for you.

🏆 Trophies will be awarded in: • Best Look-Alike • Best Pencil-Thin Mustache • Best Creative Mustache

🎖️ A People’s Choice Best of Show will be selected from the three winners. The grand prize? Two round-trip tickets on the Key West Express, a two-night stay at the Pier House, dinner for two at One Duval, a deluxe gift package from Beards & Brews, a limited-edition bottle of First Legal Agave Spirits—and the glory of holding the reigning title.

📍 Where: The legendary Chart Room Bar—where Key West’s favorite son once strummed his way into local lore

🕑 When: Registration from 2:30 to 3:00 PM | Contest begins at 3:00 PM

Expect free stick-on mustaches, photo ops, live trop rock tunes, poolside drinks, and Chart Room charm. Plus, the award-winning barbers from Beards & Brews will be onsite crafting artistic trims for anyone looking to level up their look.

Whether your ‘stache is natural or not, join us for a hilarious, hair-raising good time. Come for the fun—leave with a trophy.

A Bit About the ‘Stache

The pencil mustache—a thin line of facial hair just above the upper lip—first gained popularity in the 1930s and ’40s, worn by Hollywood icons like Clark Gable, David Niven, and Errol Flynn. Its sleek style was seen as sophisticated and suave. Jimmy Buffett gave this facial hair its own place in pop culture history with his 1974 hit “Pencil Thin Mustache.” The song is a nostalgic nod to post-war Americana, TV shows, and bygone icons, written from the perspective of a young boy who yearns for the grown-up world of mystery, coolness, and mustaches. Both tongue-in-cheek and deeply rooted in pop memory, it’s a song that celebrates the eccentric characters who helped shape our collective sense of style and swagger. And that’s exactly what this contest is all about.