Unlock Your Summer Power: The 13 Cuban Collar Shirts That Crush Boring Style and Keep You Winning All Season Long

George Feldenkreis was known as the “Guayabera King” of Miami before he acquired Perry Ellis in 1999 and expanded the brand into the full-blown conglomerate that houses Callaway, Original Penguin, and more. Cubavera, a lesser-known offshoot, was his way of getting back to basics—the four-pocket embroidered shirt that got him his start. Take your pick from long-sleeved or short-sleeved, cotton or linen, with or without pockets, with or without embroidery, and every combination between.

Two added bonuses: The brand has the best size variety on this list, and it’s available on Amazon with next-day shipping for that family vacation photo you forgot to shop for . . .

For an offbeat print that doesn’t scream “golf dad on the Atlantic City boardwalk,” check out Tombolo. This palm-inspired print barely scratches the surface of all that’s available. The brand has irreverent large-format designs like beach scenes and cocktail embroidery, classic florals, heavyweight terry towel fabrics, matching sets, and even artist collabs. For further proof that this is the brand to shop for your Euro Summer, it even dropped a mermaid-themed capsule collection with the iconic Le Sirenuse hotel in Positano.

It is said that the Cuban style made its way stateside in the 1950s. This cotton black version would’ve looked just as at home in your grandfather’s wardrobe then as it will in your wardrobe 50 years from now. It has a slightly cropped, boxy fit that leans further into the midcentury codes. And unlike some of the other options on this list, this one has potential for year-round wear.

Camp collar shirts are short-sleeved, nine times out of ten, which makes them distinctively casual. Todd Snyder knows that, and that’s why he made this long-sleeved version that’s perfectly suited for a well-dressed humid summer night.

There are two options: this lightweight soft cotton option that’s begging to be packed for your next vacation or a more traditional cotton-linen blend with subtle drop-stitching. Todd also offers his take on a traditional four-pocket guayabera.

Lululemon has gotten pretty darn good at making casual silhouettes with performance fabrics. At first glance, this looks like seersucker. Put it on, and you’ll soon realize it’s actually made of a four-way stretch that linen can’t compete with in terms of comfort. Wear it a little longer—out in the hot sun for a walk, perhaps—and the sweat-absorbing properties will come in handy. I’m sticking with a different linen shirt for dinner, but I’d wear this on a day excursion or to the airport in a heartbeat.

When you’re headed to the beach or pool, reach for a terrycloth shirt. The more towel-like it feels, the better. I have a similar style from Madewell, and I like that the vertical stripes are graphic enough to kind of distract from the off-duty fabric. In other words, you can get away with wearing it to casual dinners.

For the ultimate in camp collar relaxation, reach for a silk (or silk-blend) fabric that drapes over the shoulders and chest with enviable ease. Orlebar Brown makes some of our favorite investment-worthy swim trunks, and its accompanying collection of resortwear measures up. Here, the Portuguese silk fabric is complemented by an ornate, symmetrical paisley pattern.

The thing about silk? It’s very expensive. Viscose is a semi-synthetic alternative that achieves a similar draped fit and ventilation with a more appealing price tag. The ventilation is what separates it from considerably cheaper satin polyester shirts that will leave you suffocated (almost certainly the shiny Hawaiian you have hanging in the back of your closet).

The brand also makes a long-sleeved version for your nice night out on vacation.

Given their relaxed nature, Cuban-collar shirts aren’t the easiest style to look elegant and polished in, but this clean silhouette from Scandi-minimalist Cos begs to differ. Taking cues from the tuxedo shirt, it has cotton panels that add visual interest. Wear it on its own or pair it with a summer suit for a relaxed outdoor wedding.

Alternative dressy options include a traditional-inspired cotton long-sleeve with pintucked layers (Bode, $690) or a more tailored silhouette with embroidered appliqués on the front buttons (Manière De Voir, $185).

We’re primarily focused on quality fabrics here because the last thing you want is a shirt that makes you more sweaty than you already are when it’s hot outside. The under-$50 market gets a little dicey, but this 100 percent cotton option from old faithful Levi’s is a safe bet. The neutral color and texture on this one are pretty versatile, and the red tab on the front gives it a Western appeal that makes it feel appropriate for three-season wear.

There’s a time and place for the tropical print. We’re not hating, but we do have some tips for keeping it stylish and versatile for more than off-duty wear. Opt for monochrome or duochrome prints, asymmetrical or painterly designs, geometric patterns, embroidery, and neutrals.

St. Tropez mainstay Vilebrequin keeps it classy with a pop of the vibrant paradise plant. For more inspiration, consider J. Crew’s nostalgic East Coast map drawing ($89.50), Lands’ End’s range of medium-impact florals ($69.95–$79.95), an affordable pick in a neutral palette ($29), or the Hawaii-based brand Tori Richard ($148).