Tailwheel Shorts

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: 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: Celebrate aviation and LGBTQ+ pride with this clean, flat-vector rainbow Cessna 170 silhouette graphic. Featuring the classic profile and timeless curves of the iconic single-engine taildragger, the airframe is filled with horizontal rainbow pride flag stripes spanning from the propeller to the vertical stabilizer. Delivering an uplifting, minimalist statement of visibility, diversity, and inclusion in flight, it makes a wonderful gift or everyday apparel piece for LGBTQ+ pilots, tailwheel aviators, flight students, aviation buffs, and proud community allies alike.

Description: Celebrate the daring heritage, grassroots freedom, and golden age of pasture-hopping flight with this bold monochrome aviation graphic. Centered around rugged, arched vintage block lettering reading "BARNSTORMER," the illustration features an open-cockpit radial biplane executing a low-altitude pass with a spinning propeller blur. Grounded below by a classic countryside farmstead with a rustic barn and plowed fields, this nostalgic design pays tribute to the 1920s daredevils who brought the wonder of aviation straight to rural America. It makes an inspiring gift or everyday apparel staple for vintage biplane pilots, tailwheel flyers, aircraft restorers, airshow fans, and classic aviation enthusiasts alike.

Description: Celebrate aviation and intersectional LGBTQ+ visibility with this clean, flat-vector Progress Pride Cessna 170 silhouette design. Featuring the classic profile of the iconic single-engine taildragger, the airframe is filled with horizontal rainbow pride stripes and accented forward with the Progress chevron—showcasing transgender pride colors alongside black and brown stripes across the nose cowl and propeller. Delivering an uplifting, minimalist statement of diversity and inclusion in flight, it makes a perfect gift or everyday apparel piece for LGBTQ+ pilots, tailwheel aviators, flight students, aviation enthusiasts, and proud community allies alike.

Description: Celebrate general aviation and transgender visibility with this dynamic retro flight graphic. The design features the classic high-wing silhouette and wheel-pants profile of the iconic Cessna 170 taildragger banking smoothly into flight, reimagined entirely in the pastel blue, pink, and white stripes of the Transgender Pride flag. Accented with detailed wing struts, crisp panel line work, and a spinning propeller blur ring against a dark backdrop, this artwork pairs vintage general aviation style with an uplifting statement of trans pride, courage, and authenticity in the sky. It makes a standout apparel piece and meaningful gift for transgender pilots, tailwheel aviators, flight students, flight instructors, and proud LGBTQ+ community alli

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

Description: Celebrate the daring spirit, golden age romance, and grassroots freedom of early flight with this clean, vintage-inspired aviation graphic. Framed by elegant classical serif lettering declaring "BARNSTORMER," the design is crowned by a detailed illustration of an open-cockpit radial biplane banking sharply overhead with a spinning propeller blur. Paying tribute to the 1920s daredevils, pasture-hopping aviators, and the pure adventure of open-cockpit flight, this sharp monochrome design makes a timeless apparel piece and ideal gift for vintage biplane pilots, tailwheel flyers, aircraft restorers, and classic aviation enthusiasts alike.

Description: Celebrate general aviation and LGBTQ+ visibility with this clean, horizontal flight graphic. The illustration showcases the classic side profile of the beloved single-engine Cessna 170 taildragger rendered over a distressed Progress Pride flag banner. Featuring the inclusive Progress chevron across the cowl and propeller—highlighting transgender pride colors alongside black and brown stripes for marginalized communities—this design delivers a clear message of inclusion, pride, and solidarity in the skies. It makes a wonderful statement piece or gift for LGBTQ+ pilots, tailwheel aviators, flight students, and proud community allies alike.

Description: Celebrate the daring heritage, open-cockpit freedom, and grassroots adventure of early flight with this classic monochrome aviation graphic. Crowned by head-on illustrations of two antique radial biplanes flying in formation, the design is anchored below by elegant vintage serif typography declaring "BARNSTORMER." Showcasing the exposed struts, tensioned bracing wires, two-blade wooden propellers, and rugged landing gear of golden-age aircraft, this timeless artwork pays tribute to 1920s daredevils and grass-strip aviators. It makes an inspiring gift or everyday apparel piece for vintage biplane pilots, tailwheel flyers, aircraft restorers, airshow fans, and classic aviation enthusiasts alike.

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,