GREAT GUAYABERA: A NOD TO VIPR FRIENDSHIP & FASHION

Former senator and current St. Croix Administrator Sammuel Sanes, left, is seen wearing a custom guayabera with traditional USVI madras striping down the front at the VIPR Friendship Day Commemoration held Oct. 9 at Government House, St. Croix. Photo courtesy of Government House- US Virgin Islands/Facebook.

As a little girl growing up on St. Croix, I remember seeing my Trinidadian father dressed in these shirts all the time. Mom always had them freshly washed and pressed, and he would either be wearing a white one, a light green one or a light brown one any given day. I always thought he looked so distinguished in them.

Then, there was our older Puerto Rican neighbor, Mr. Rosario, who would wear the shirts whenever he and his family were headed out or sometimes, he would walk around his front yard tending to his plants with the shirt unbuttoned while wearing a white vest underneath, catching a breeze. And my Uncle Gerry, who is age 103, by the way, still wears them at home and when he’s out running errands with his caretaker in Frederiksted. Many of you might have fathers or grandfathers that wear (or wore) these shirts, too.

I’m talking about the guayabera—a men’s fashion staple in Latin America, the Spanish-speaking Caribbean, Mexico, and throughout many English-speaking Caribbean islands, like the USVI. The shirt’s style is distinguished by its loose fit designed to be worn untucked, and four front pockets with tiny pleating on both the garment’s front and back. Guayaberas are often made from linen or cotton, ideal for wearing in warm temps, and come in long or short-sleeved styles.

The research is mixed among scholars on the origins of the guayabera, with findings pointing to possible origins in either the Philippines, Mexico or Cuba.

I mostly remember older men in my life wearing guayaberas, the name they are called in Puerto Rico (they have different names in other parts of the world); however, guayaberas are having a pop culture moment in 2025, thanks to millennial international music superstar Benito Antonio Martínez Ocasio, AKA, Bad Bunny. The Puerto Rican rapper, singer and record producer—who will perform the Superbowl Halftime Show in Jan. 2026—has been intentionally keen to express and celebrate his Puerto Rican identity through wearing custom-made guayaberas for many high-profile events this year, including  the release of his Debí Tirar Más Fotos album in January, as well as during his history-making, 30-show residency that ran from July-September at Puerto Rico’s El Choli arena.

Custom guayabera worn by Bad Bunny during one of his residency performances this summer in Puerto Rico. The shirt was made by Puerto Rico-based design house YAYI, namesake of Puerto Rican designer, Yayi Perez. Photo courtesy of YAYI/Facebook.

The USVI commemorated the 58th anniversary of Virgin Islands-Puerto Rico Friendship Day on Oct. 13 during the annual national celebration of Hispanic Heritage Month, Sept. 15-Oct. 15. VIPR Friendship Day highlights the shared culture, history and familial ties between the Virgin Islands and Puerto Rico. During this year’s celebration, held at St. Croix Government House on Oct. 9, some guests were spotted wearing the beloved guayabera. It was the perfect choice for the occasion, as the garment can be worn for both formal and informal gatherings.

I don’t know if guayaberas were first introduced to the Virgin Islands with the mass migration of residents from Vieques to St. Croix that began in the 1920s and lasted through the 1960s. Nonetheless, how ever the garments got here, I’m sure glad they did! So, whether you’re a gentleman of Crucian, Puerto Rican, Crucian-Rican or other Caribbean descent, your style will always be topnotch when you pull on a guayabera.

Here’s to another year of great friendship and great fashion between the Virgin Islands and Puerto Rico!