There is an old adage that says, “The clothes make the man.” Well, in Tampa come late January, the clothes make the pirate. During the annual Gasparilla festival and parade, dozens of colorful krewes make their way down Bayshore Boulevard to downtown Tampa. Each krewe wears a costume that symbolizes its history and culture, from Spanish knights to Rough Riders, Caribbean revelers, and, of course, pirates. Of all these, the original krewe and founders of the celebration, Ye Mystic Krewe of Gasparilla, are the only ones whose costumes have substantially evolved and changed over the years.

When Ye Mystic Krewe first invaded Tampa in 1904, they did so in rented Mardi Gras costumes from New Orleans. They continued this tradition for the next few years until the Krewe took a three-year break beginning in 1907.
The Krewe and the Gasparilla parade returned in 1910, and it was around that time that the organization began supplying costumes for its members. These costumes were similar to Mardi Gras attire, appearing more formal than what a typical pirate might have worn. Although pirate imagery was becoming common in popular culture thanks to artists like Howard Pyle, the pirates of Ye Mystic Krewe looked more like Three Musketeers than characters from Treasure Island.

This remained the case through the mid-1920s, but by the late 1920s or early 1930s—possibly due to an influx of new members in the ‘20s or the economic pressures of the Great Depression—the pirates began creating their own costumes. These outfits became more individualistic, colorful and less formal.

The Krewe paused the annual Gasparilla celebration during World War II, as many members, along with millions of other Americans, donned more official uniforms. When the Krewe and parade returned in 1947, Ye Mystic Krewe continued to embrace the rougher, if not more authentic, look of pirates rather than courtly knights.

Pirate costumes in the 1950s followed this tradition. Oral histories and old photographs suggest that many Krewe members incorporated elements of their everyday business attire into their costumes. For example, suit vests and pants were often cut and trimmed in contrasting fabrics to mimic the look of a daring buccaneer. Shirts were oversized and blousy, made from colorful fabrics, while bandanas—which first became popular in the 1920s—were still very popular. Boot tops (fake boot uppers worn over street shoes) were common, and grease pencils were used to draw scars and black eyes to round out the look.

While the basic pirate look remained consistent through the 1960s, one new element gained popularity—the feathered hat. Parade photos from the time show their increasing prevalence, though bandanas were still the more common headwear. Another change was the vest, which by the 1970s was being custom-made for pirate costumes with a slightly larger cut.

The current look of flash and feathers solidified in the 1970s and early 1980s. Today, hats, krewe pins, boots (rather than boot tops), custom-made buttons and elaborate embellishments round out the modern pirate look, along with much more elaborate and professional makeup. The goal is to stand out while remaining anonymous, which, when reflecting on the history of pirates, stays true to tradition.
Rodney Kite-Powell is a Tampa-born author, the official historian of Hillsborough County and the director of the Touchton Map Library at the Tampa Bay History Center, where he has worked since 1995.
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