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Our Favorite Cigar Shirts

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Holt's Staff

When you’ve got a brand you’re dedicated to, it’s easy to pull the trigger on a ball cap or a shirt with the company’s logo. Now that the weather is warming up, having a surplus of T-shirts is great for last-minute trips to the beach or impromptu barbecues. A lot of premium cigar-makers offer shirts, hats, and other apparel that advertise their brands. There is even a certain style of shirt, the guayabera, which is often associated with cigar-makers and enthusiasts due to its widespread popularity in the Caribbean and a number of cigar-making countries. When you want to show your pals you’re a fan of fine cigars with a cool and comfortable cigar shirt, here’s a quick rundown of some of our favorite picks.

Enter the Guayabera: A Little Bit of History

Like the definitive smoking jacket, the cigar shirt has a history all its own. While a silky smoking jacket fits in perfect in a tufted leather armchair in front of the fireplace or a night out when you can’t hide your Rat Pack mentality, the guayabera bears some impressive hallmarks for traditional lovers of premium cigars. 

Sometimes referred to as a Mexican wedding shirt, the guayabera actually has Cuban roots. This classic, lightweight, collared button-down cigar shirt is distinguished by two vertical rows of strictly sewn pleats that run down the front and back of the shirt for needed ventilation in hot or humid weather. (After all, we’re talking about Cuba where staying comfortable in “caliente” temperatures is critical.)

Although the general style of the guayabera remains the same, there have been slight variations over the years. Some shirts have long sleeves with cuffs, while others favor a shorter sleeve cut off at the elbow. To keep things cool (in more ways than one), the guayabera is typically constructed of cotton or linen in light colors, ranging from bright whites, soft eggshell tones, or pastels. Today, the shirt can be found in its classic hues as well as brighter tones and even black. 

During the 1950s, the Cuban cigar shirt rose in popularity in North America thanks to celebrities like Ernest Hemingway. A number of leaders, including Fidel Castro, César Chávez, and U.S. Presidents Ronald Reagan, George H.W. Bush, and Barrack Obama have worn guayaberas to echo the shirt’s political symbolism or to express inclusiveness of its underlying message. Its perception has been aligned with a populist agenda, traditionally. The shirt’s formal comfort and historical significance perpetuate its popularity among cigar lovers today. Today, it’s common to see renowned cigar-makers like Carlito Fuente and Jose ‘Pepin’ Garcia wearing the iconic shirts, often with a handful of mouthwatering cigars tucked into the neat pockets.

Casual Wear for the Cigar Connoisseur

Maybe you’re looking for something that bridges the gap between casual and formal a bit more when you feel like playing a round at the local country club or you’re headed to a company picnic. The Ashton ‘Clubhouse’ Dry-Fit Polo is a great option. Soft, breathable material and a silky black sheen marry classiness and comfort for any occasion. 

Discover the epitome of practicality for diehard cigar lovers with a cigar pocket shirt – in some cases, a simplified take on the guayabera. You can find them designed as button-down shirts as well as in a polo style. Bottom line, fashion meets function on any shirt that flaunts a dedicated cigar pocket. Some come with up to 3 or 4 cigar pockets or feature individual pocket-sleeves for every single cigar you feel like toting around.

But if you’re looking for something that’s straight-up casual and simple, proudly proclaim your loyalty to your favorite brands like Ashton, La Aroma de Cuba, and San Cristobal with a colorful and comfy selection of cigar T-shirts.

Show your love for a bestselling brand with the Ashton ‘Classic Crown’ collection, or checkout the La Aroma de Cuba ‘Ancients’ V-neck Tee, for a hip, laid-back look that celebrates a popular Cuban-legacy label.

And let’s not forget about those cigar lovin’ ladies who like to sport their affinity for premium smokes. Vivid, form-fitting styles are as cool as they are comfortable in the Ashton Symmetry Woman’s Tee with the brand’s intricate butterfly design, or a relaxed San Cristobal ‘Beach’ Women’s Tee in a lavender color.

Celebrate your cigar obsession with a T-shirt from a number of celebrated brands. Casual, comfortable, and fashionable options look great when you’re heading to the beach, the park, or a simply the backyard hammock. 

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