Honoring Mary Ann Carroll First Lady of the Highwaymen

The Orlando Pride women’s professional soccer team introduced the Highway Woman Kit, the Club’s 2023 primary jersey, influenced by and paying tribute to Mary Ann Carroll first lady of the Highwaymen. The kit – uniform – was designed in collaboration with the estate of Carroll (1940 – 2019), a legendary Black artist and the only woman of the iconic original Florida Highwaymen painters group.

The Highway Woman Kit is now available for purchase at ShopOrlandoPride.com or at The Den at Exploria Stadium.

“Our Club takes great pride in using our kits as a platform to share and elevate the stories of barrier-breaking women from our community” Pedro Araujo, chief marketing officer for the Orlando Pride, said. “Mary Ann Carroll was one of Florida’s most talented historymakers, and we’re honored her family has allowed us to pay tribute to her and share her inspiring story with our fans and the soccer community through this kit.”

Beginning in the 1950s, an era of the Jim Crow South and segregation, a group of Black young people became the original Highwaymen – six self-taught and self-mentoring artists who traveled throughout the state of Florida, painting and selling landscapes out of the trunk of their cars, as galleries would not feature the work of Black artists. Mary Ann Carroll first lady of the Highwaymen was a member of that original troupe and the only woman in the group that grew to 26.

Together, through 30 years of painting and battling racial discrimination, it is estimated that the Highwaymen created over 200,000 works of art. They were later inducted into the Florida Artists Hall of Fame in 2004.

The Florida Highwaymen were never formally connected as a group, many members had zero connection with each other; the name came about when Florida art historian Jim Fitch created it in 1994, attempting to give the African American landscape painters working along the Atlantic Coast selling their paintings door-to-door and by car a collective designation.

Mary Ann Carroll with her paintings.
Mary Ann Carroll with her paintings. Courtesy of the artist’s estate and Orlando Pride.

“When the Pride approached me about this collaboration, it was an easy ‘yes,’” Carroll’s daughter, Dr. Wanda Renee Mills said. “My goal is to continue sharing and speaking of my mother’s legacy and the impact she made here in Florida. She was a fierce competitor who loved sports and loved seeing women succeed.”

Mary Ann Carroll first lady of the Highwaymen, moved to Fort Pierce one town south of Vero Beach on the state’s Atlantic Side from Georgia at 9-years-old. As a teenager, she met Harold Newton, the “first” of the original Florida Highwaymen painters and the group’s defacto figurehead.

Newton, not surprisingly, was painting a poinciana tree when Carroll met him, and, intrigued, wanted to try herself. It is believed Newton helped young Mary Ann Carroll with her first painting at which point she was off and running. After sharpening her skills, she took to the highways in a 1964 Buick Electra, traveling as far as Miami to the south and Jacksonville to the north.

Remember, this would have been in the 1960s and ‘70s in Florida, the Deep South (don’t let anyone tell you different), an all-to-often dangerous place for Black people, and she was a Black woman, traveling alone. That in itself took guts.

Highwaymen Art Specialists

“The Pride players embody my mother’s spirit, and it was an honor to not only meet them, but work alongside them on this project,” Mills added. “My mother always reminded me, ‘I won’t be painted in a box, I’m too strong and talented for that,’ and these are players that will never allow themselves to be painted into a box. I’m very excited to see the team in these purple jerseys, her favorite color, on the field this season.”

The Highway Woman Kit reintroduces an all-purple look for the Pride, with a dark purple base for both the jersey top and the shorts. As a nod to Carroll’s artistry, the main pattern of the kit is highlighted by a contrasting, lighter purple brushstroke pattern.

Inspired by the Fort Pierce native’s landscape work, the bottom of the kit features an embellishment displaying a silhouette of a Royal Poinciana tree – a favorite and familiar motif of her art – and Carroll’s signature. Returning to a full-color woven Pride crest, the Club’s Eola Blue color is also carried down into the embellishment.

Orlando Health, the team’s presenting and official medical team, is proudly displayed across the front of the jersey, marking the eighth-consecutive season of partnership with the Club.

The kit was unveiled on Wednesday, March 22, 2023, at the “Queen of the Road” event in downtown Orlando which showcased many of Carroll’s artwork and items from her personal collection. The event allowed Carroll’s work to be showcased in a gallery – something that was not afforded to her or the rest of the Highwaymen during their early days – in the heart of Parramore, Orlando’s oldest, historically Black neighborhood.

The complete 2023 Pride roster attended the event as well as Mills, who not only appeared in the Club’s jersey unveil video but also provided Carroll’s easel, art caddy, handwritten color wheel and her final, unfinished painting as props for the video.

The City of Orlando further commemorated Mary Ann Carroll first lady of the Highwaymen in 2022 using one of her paintings for a massive, 20-foot-tall, digital projection in the newly opened Orlando International Airport Terminal C.

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