Every summer, or whenever traveling somewhere tropical, I look forward to donning my favorite hot-weather garment: a bespoke guayabera I picked up in Texas. Hands down, this airy button-down is a piece-de-resistance of my wardrobe. Like a sharp leather jacket, you just feel badass wearing a guayabera—think Hemingway in a cafe in Cuba, or Hunter S. Thompson at a watering hole in Puerto Rico.
I bought my first guayabera during San Antonio’s Fiesta, the riotous, annual celebration of the Mission City’s colorful cuisine, music, and culture. Braving the crowds of the Riverwalk to watch the boat parade, I started shooting the shit with a fellow reveler. Clearly a character, my new friend sported epic Fiesta getup: colorful sombrero, Spurs face paint, and a curious shirt with ornate embroidery and four frontal pockets. Even half-drunk and covered in paint, my man looked pretty damn dapper with that shirt, I had to admit. A pair of cigars poked out of a breast pocket and a flask rested in a lower one, and, in a gesture of high Southern hospitality, he offered me a stogey and nip of whisky as we watched the water-borne concert. Right then and there, I knew I wasn’t departing Texas without acquiring such a garment, this sartorial jack-of-all-trades.
History of the guayabera
While now considered luxury apparel, the guayabera has humble roots in the fruit orchards of Spain and Latin America. The quadri-pocket design initially served a utilitarian function: allowing farmers to easily port freshly picked fruit. Especially in Cuba, the cargo in question was usually guava, hence the shirt’s moniker. Depending on where you are, the guayabera might go by other names—a Mexican Wedding Shirt in Texas, a Hemingway shirt in South Florida.
Nobody is exactly sure where the garment originated, with competing theories claiming Spain, Mexico, or the Caribbean. Mirroring the evolution of jeans in the United States, the shirt eventually morphed from proletariat workwear to upper-crust leisurewear. As the style crossed from dirt fields to polo fields, rough cotton fabric got swapped out for luxurious linen or silk. Creative seamstresses added elaborate embroidery like Arabesques, pinstripes, and, especially in Mexico, ornate floral patterns. Frontal pleats added an extra dash of flourish and dressiness.
Modern guayaberas are versatile—looking equally debonair at weddings, cocktail bars, or cookouts. They’re fantastic travel shirts, the frontal pockets ideal for toting a passport, plane tickets, or a book. Caroline Matthews, the owner of Dos Carolinas, a legendary San Antonio boutique, claims they even make handsome tuxedo shirts. “If you look at old photos from Cuba, you’ll see guys wearing guayaberas with tuxedo pants and bowties,” she says. But since the shirt is meant to replace a formal jacket, you should rock it sans blazer or suitcoat.
Want to look like a million bucks at a beach party or outdoor gala? Guayaberas pair fantastically with shorts and loafers. In late spring in New York City, I wear mine with jeans or khakis and a pair of Red Wing boots. In Texas, you’ll commonly see guys sporting them with bolo ties (another woefully underrated masculine accouterment).
Where to buy a great guayabera
If you spend enough time in Houston or San Antonio, you’ll inevitably come across Dos Carolinas’ beautiful handiwork. While the prices are a splurge ($220 for off-the-rack shirts, and close to $300 for bespoke shirts), Dos Carolinas stitches the luxury guayabera par excellence. Caroline and her tailors carefully select the highest-quality linen, silk, and wool to craft these breezy, handsome button-downs.
Keep in mind that Dos Carolinas’ guayaberas cleave to the traditional style—a fuller, boxier cut meant to fit loosely and keep the wearer cool. However, if you absolutely need to broadcast the chiseled bod, Caroline’s got you covered, too: “I get that some guys want to show off their broad shoulders and narrow waist,” Matthews says. “If you go with a customized guayabera, we can tailor a more form-fitting cut.” If you opt for customized, you choose the fabric, cut, and the embroidery’s pattern and colors.
Dos Carolina’s flagship store is in San Antonio, but they also have a location in Houston’s posh River Oaks District. And if you aren’t planning to drop by Texas any time soon, Caroline also ships guayaberas all over the world. If you have your exact measurements handy, they can even nail custom orders over the phone.
Penner’s has been a beloved San Antonio haberdashery for over a century. Founded by Morris Penner, a Jewish immigrant from Poland, Penner’s sells traditional guayaberas (~$175 a pop) in a wide range of colors and styles. In contrast to traditional white guayaberas, Penner’s carries guayaberas in festive hues like burnt orange, indigo, and onyx. My favorite is their silk guayabera with embroidered roses along the pockets (yes, you’ll feel like Zorro when wearing it). To complement your razor-sharp guayabera and complete your dashing caballero fantasy, Penner’s also carries beautiful selections of Panama hats, men’s jewelry, and footwear.
San Cristobal, another Texas-based clothier, takes its name from the patron saint of travelers. The idea to craft functional clothing for stylish wayfarers came to Paul Hotze, San Cristobal’s founder, during a motorcycle odyssey from his native Houston to the Tierra del Fuego in Argentina. Hotze grew up wearing guayaberas but wanted to create a travel shirt with appeal beyond the Lone Star State. “A lot of the guayaberas you buy in Texas have these in-your-face Texas symbols,” Hotze says. “That’s fine, but I wanted to make a more universally marketable guayabera.”
San Cristobal shirts come in several distinct styles. The El Guapo line offers slender-cut shirts, giving wearers a more form-fitting guayabera. El Presidente shirts are more conservative, what Paul describes as “an entry-level guayabera, for those who don’t want all the loud embroidery and pleating.” In contrast, the Hemingway line, in honor of the knockabout man of letters, embraces flamboyant embroidery and vivid colors. San Cristobal, while based in Houston, ships all across the U.S.
San Antonio’s Historic Market Square
If you’re up for an adventure, you might find smoking bargains around San Antonio’s Historic Market Square, the open-air fair locals simply call El Mercado. Among the endless assortments of artwork, spices, and Texas-themed tchotchkes, vendors hawk guayaberas imported from Mexico. While you won’t find the range of sizes and styles of the shops above, El Mercado’s price-to-quality ratio is excellent. I bought a gorgeous, linen guayabera in El Mercado for around $70—one of my best sartorial scores of the past year.
Vendors are usually amenable to some light haggling—who knows, maybe a kindly merchant will throw in one of those cowboy-boot shot glasses or “Don’t Mess With Texas” coffee mugs with your guayabera. And after your shopping spree in El Mercado, make a beeline for Mi Tierra, a San Antonio landmark arguably serving the world’s best Tex-Mex.
For dashing hot-climate apparel, you can’t beat a high-quality guayabera. The distinctive shirt adds a level of panache surpassing a traditional button-down or polo shirt. While good guayaberas are expensive, they will last years with proper care. The extra pockets are uber-handy when on the go, making for a nonpareil travel shirt. To keep your guayabera looking crisp and clean, Caroline Matthews recommends washing them with cold water and air-drying them. Dry-cleaning from time to time is perfectly fine, too.
Lead photo credit: San Cristobal