Tailwheel Hats

Description: How do you know someone is a taildragger pilot? Oh, they'll tell you :) Might as well wear the T-shirt

Description: Our retro yellow "Tailwheel Pilot" shirt, designed like the gas station uniforms of old. Wear it proudly!

Description: Tell everyone how you feel about flying tailwheel airplanes. That's right, you feel awesome!

Description: Capture the essence of tailwheel and backcountry flying with this design.

Description: How do you really feel about tailwheel flying? The few, the proud, the tailwheel pilot... Tell the world

Description: Vintage flag design featuring the iconic Piper J-3 Cub. Could also be used to represent the PA-18 Super Cub. Distressed graphics for a vintage look.

Description: This is the 1947 Cessna 140 ad that advertised one of the most successful general aviation airplanes in history. The Cessna 140 went on to dominate the aviation world with over 7000 built and many still flying. This ad captures the vibe of that era. Wear it proudly. Cessna Logo on front as well

Description: Fun Aviation design for pilots and aviation enthusiasts alike.

Description: This design is made from the period-correct, authentic Cessna art, including the correct logo. It is the same one from the 1940s. This features the classic Cessna 140 with its "unofficial moniker of, "MiniWagon," which is a nod to its bigger brother, the Cessna 180.

Description: Custom illustration of a classic taildragger airplane.

Description: A vintage style design featuring the iconic Piper PA-18 Super Cub.

Description: Fun design for pilots that fly a Turbine Stol Tailwheel Airplane

Description: Are you a REAL pilot?

Description: Celebrate the legacy of the Cessna 170 with this minimalist vector illustration. As the direct predecessor to the iconic Skyhawk, the 170 is cherished by pilots for its classic taildragger configuration and vintage charm. This high-contrast design highlights the clean lines and timeless appeal of this beloved general aviation aircraft. A perfect tribute for aviation enthusiasts, tailwheel pilots, and collectors of historic aircraft art who value the history behind the flight.

Description: Vintage style design featuring the classic J-3 Cub airplane. Distressed for a vintage look.

Description: Fun design for pilots that fly light STOL Tailwheel Airplanes

Description: Fun design for pilots and aviation enthusiasts

Description: Taildragger enjoying clear skies.

Description: Rans RV7 Tailwheel Aircraft for Pilots

Description: This retro, vintage-aviation inspired design features the classic PA-22 Tri-Pacer airplane. Distressed graphics for a great vintage look.

Description: This stylish design features the classic J-3 Cub airplane in it's iconic yellow paint scheme and text, "Live to Fly". Graphics are distressed for a great vintage look.

Description: Illustration of the Wag-Aero Wag-a-Bond. The Wag-a-Bond is a kit built replica of the Piper Vagabond airplane.

Description: Hand drawn Cartoon Art of the historic Mew Gull Aircraft , The Percival Mew Gull was a British racing aircraft of the 1930s. It was a small, single-engine, single-seat, low-wing monoplane of wooden construction,