The Florida Highwaymen began painting in the 1950s and 60s with one goal: to make a living through art at a time when Black artists had few opportunities in the mainstream market. Their strategy? Create bold, captivating Florida landscapes quickly and sell them directly to the public—often by knocking on doors or loading them into the trunks of their cars and traveling the highways. But over time, these quick-sell paintings evolved into a recognized art form that now commands serious attention from collectors and historians alike.
From Fast Production to Fine Art
In the early days, speed and affordability were everything. The Highwaymen painted on inexpensive Upson board (a type of fiberboard), used house paint or oil-based paints, and framed their work with crown molding they nailed and painted themselves. The goal was to produce several pieces a day—sometimes as many as ten or more—and sell them to passing tourists, homeowners, or business owners at a low price.
Their technique was instinctual and energetic. Brushstrokes were bold, skies were filled with glowing oranges and pinks, and palms swayed in breezy compositions that captured the feel of “Old Florida.” These weren’t highly detailed works, but they were emotionally evocative and instantly recognizable.
As time went on, many Highwaymen artists began refining their techniques. Some switched to higher-quality materials like canvas and artist-grade oil paints. Others took more time with each piece, layering color and detail in ways they hadn’t during the group’s early years.
Shared Style, Individual Voices
While each of the 26 original Highwaymen had their own voice, there were common stylistic elements that unified their work:
• Bright, saturated colors
• High-contrast lighting, especially in sunrise and sunset scenes
• Fast, sweeping brushwork
• Repetitive yet varied subject matter like poinciana trees, cabbage palms, rivers, and marshes
These features weren’t just artistic choices—they were practical ones, allowing the artists to work quickly while developing a brand-like consistency.
Artistic Growth and Legacy
As their reputations grew, so did the value of their paintings. What once sold for $25 on the roadside might now fetch thousands at auction. And with that shift came an evolution in technique. Later works from some artists show increased attention to composition, balance, and brush control. While still rooted in the spontaneous energy of the original movement, the art matured over time. Restorers and curators today are tasked with preserving these pieces without losing their raw character. It’s a challenge that involves honoring the Highwaymen’s roots while also recognizing the technical growth in their later years.
Final Thoughts
The Highwaymen may have started with humble tools and roadside sales, but their evolving techniques reflect decades of adaptation, creativity, and perseverance. Today, their work is not only a window into Florida’s natural past—it’s a testament to artistic resilience and innovation.