The origin of the garment is disputed, as various claims for the distinctive style have been made in several Latin America countries as well as the Philippines. In fact, every country that has produced its own version of the shirt makes some form of claim to its origins, or of adding to its origins. Some Latin Americans believe guayaberas are of Cuban, or at least Caribbean, origin. Others are certain it is of Mexican origin.
Versions of the shirt's origins claim that Mexicans either originated it in the Yucatán Peninsula or were inspired by the design of similar shirts sold in Cuba. One theory holds that it was during the era of trade routes through the Caribbean that the Mexican shirts got to Cuba, and were taken to the Philippines by the Spaniards, where the evolution of the intricate embroidery started. Alternatively, others speculate that the shirt, which has documented origins in the Philippines prior to the arrival of the Spanish, made its way to Cuba through Mexico via the Manila-Acapulco galleon trade. The origin of the Guayabera shirt remains a mystery, and a similar prototypical shirt has existed since the 18th century, probably imported from Spain.
The origin of the name is said to be either Mexican or Cuban. Guayabera may come from a Cuban legend that tells of a poor countryside seamstress sewing large patch-pockets onto her husband's shirts for carrying guava (guayabas) from the field. Guayabera may also have originated from the word yayabero, the singular nickname for those who lived near the Yayabo River in Cuba.
The guayabera shirt is distinguished by several details: either two or four patch pockets and two vertical rows of alforzas (fine, tiny pleats, usually 10, sewn closely together) running along the front and back of the shirt. The pockets are separately detailed with identical, properly aligned alforzas.
The top of each pocket is usually adorned with a matching shirt button, as are the bottoms of the alforza pleats. Vertical rows of adjusting buttons are often seen, one on each side, at the bottom hem. While most versions of the design have no placket covering the buttons, a few newer designs do.
The bottom of many shirts has three-inch slits on either side, and these include adjusting buttons. The bottom has a straight hem, thus it is not tucked into the trousers.
Though traditionally worn in white and pastels, guayaberas are now available in many solid (and loud) colors. Black guayaberas, embroidered with colorful flowers and festooned with French cuffs, have for many decades been extremely popular in Mexico. In Mexico, Dominican Republic, Puerto Rico and Cuba, guayaberas are part of the traditional wear for men.
In Zimbabwe, the short sleeve version is worn for special occasions. The shirt was brought to Africa by Cuban teachers who once lived there. Today, it has replaced the safari suit for special occasions. White shirts are worn with black dress pants to weddings, and black shirts are worn to funerals.
The guayabera is worn as office and loose formal wear all over the world. In Zimbabwe and Britain the guayabera is called a Safari shirt. In Jamaica it is known as a bush jacket; in the United States, Trinidad and Guyana, a type of guayabera (similar to a safari shirt) is sometimes called a shirt-jac; in the Dominican Republic it is known as chacabana.
The shirt-jac (also known as a "jac" for short, or a "summer jac") has become a popular clergy shirt in the last thirty years. These shirts are simpler than a guayabera, avoiding the design details such as pleats. Many clerics purchase fine guayabera shirts and have the collars re-tailored into clergy collars.
Popularity in the United States 
The guayabera rose to popularity in the United States in the 1970s when a Cuban exile named Ramón Puig brought the design with him. Designing and manufacturing them in the heart of the Cuban community in Miami, the shirts became a hit in the Cuban community and the Miami area in general. 
In the distant past, while guayaberas were typically associated with older men, they were worn by all ages. When retro clothing styles began resurging in recent years, the American consumer base shifted to a significantly younger audience.
Guayaberas are also worn at beach and destination weddings. Many in the United States enjoy Guayabera shirts due to their comfortable and elegant features. Most especially popular fabrics are the 100% linen and the 100% cotton.
In some countries and in several areas of Florida, the guayabera is often an acceptable form of office wear due to the hot weather.
The guayabera shirt is a long-standing symbol of solidarity amongst Hispanics living in America. On September 24, 2010 a powerful statement (about the guayabera as a Hispanic laborer's "uniform") was made by United Farm Workers President Arturo Rodriguez. Appearing as a primary speaker at a U.S. Congressional Subcommittee hearing on Immigration, Citizenship and Border Security, President Rodriguez wore a finely tailored guayabera.
Guayaberas were worn by over 20 lieutenant governors attending a National Lieutenant Governors Association meeting in Puerto Rico in 2011.
Similar shirts 
British and Americans have been wearing versions of the Guayabera for many generations. Known as "safari shirt" in Britain and "camp" (or "jac") shirt in America, their popularity first became quite notable in the 1930s. As in the Caribbean countries, Americans found the shirt to be acceptable office/business wear during extremely hot weather. Previously, Americans had only worn such shirts during their leisure time. In the UK (especially the colonies) and America, a plain form of safari shirt also became popular.
The real "safari shirt" is usually made of stronger material (less light weight), and has gussets in the back to provide more flexibility. This shirt has upper pockets. The safari shirt is confused herein with a safari jacket/bush jacket which is a single layer, long sleeved and long square tailed affair often made iconic by film directors and seen in photos of Ernest Hemingway. The jacket has lower open pockets and is worn open (not buttoned); it sometimes serves as a photographer's jacket. Both shirt and jacket signature color is tan.
Clergy shirts, as a variant of the British safari, have been worn for many decades and are common.
One of the Philippines' national costumes for men, the Barong shirt has some features which are similar to the guayabera. However, the Barong Tagalog is a much more formal piece of clothing. It lacks pleats or pockets, and is marked by intricate, hand-sewn embroidery in a variety of forms, including geometric or floral patterns. It is not made of linen, but rather of hand-woven, fine, translucent pina or jusi fiber. 
In the Samoan islands the shirt style has been introduced into the masculine formal attire known as the "safari set". American Samoa's version of the shirt often includes tightly-sewn vertical pleats and two or four buttoned pockets.
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- Congressional Subcommitte Hearing on Immigration, Citizenship and Border Security, C-SPAN 3, 24 September 2010
- pp.5, item #944