Best Cuban Collar Shirts and How to Wear Them

The best Cuban collar shirts – also referred to as a camp, cabana, or revere collar shirt – have transformed from strictly retro wear into a men's wardrobe staple. Call it a convenient slice of Americana.

Or, sport one to attempt the relaxed-but-structured, wider-cut trend that’s been gradually overtaking menswear. Beyond the obvious, the silhouette has a near-ubiquitous presence today, from all those on-trend Hawaiian shirts to the traditional guayabera.

Cuban Collar by Prada

What is a Cuban Collar Shirt?

A handful of key features define the Cuban collar shirt. One, it has to have a loose and straight, if not boxy, fit falling to the hips – nothing slim or with a shirttail hem.

Secondly, a double-notch, one-piece collar is the most definitive aspect. Traditionally, you could wear it open and spread out – alone or over a jacket – or closed at the neck with a button and loop.

Cuban Collar Shirt by French Connection

History of the Cuban Collar Shirt

From a strictly western perspective, the shirt appeared in men’s wardrobes in the early 20th century as a casual, warm-weather style, occasionally called a “negligee” shirt for its lack of starch and tie.

At the time, in both the U.S. and U.K., stiffer, wrinkle-free garments with angular collars characterized everyday dress. Yet, garments resembling the Cuban collar shirt date back much earlier than that.

Although the exact location and date are disputed, the silhouette started appearing as a working-class men’s staple in South America and the Caribbean in the 18th century.

The relaxed design and softer material were better suited to working outdoors in the heat. As well, many of these earlier designs incorporated pockets for storage – now a staple of modern-day work shirts.

In the United States, however, the style found its footing as a “sport shirt” or “vacation shirt” – general terms applying to casual pieces like polos and T-shirts and a more accessible look seen on the period’s leading entertainers.

Advertisements, on the other hand, branded the look as a “convertible collar” shirt: Specifically, the garment lacked the traditional stand piece, resulting in a flat collar.

Yet, unlike today, you could still button the collar all the way up, letting you wear it with a necktie if needed. As well, as a way to differentiate it from regular dress shirts, the “loop collar” shirt made its way into the period’s lexicon. 

Cuban Collar Shirt by Antony Morato

Early 20th Century

Yet, while the ‘50s-era design sets the stage for today’s shirts, the collar went through a few changes during the first half of the 20th century. For the first few decades, the collar held the same angular, spearpoint shape: picture a traditional dress shirt without a collar stand.

The collar style, too, tended to be wider than later varieties and often had more of a teardrop shape. Additionally, up until the 1930s, casual shirts didn’t usually feature a loop collar.

Cuban collar by Reiss

Cuban Collar in the 1950s

By the ‘50s, the shirt took on its familiar shape: a smaller, more angular collar with a clear double-triangle shape. Not long after, the top loop fell out of favor.

The collar and fit weren’t the only innovative features at the time. First, because of the draped shape, clothing stores sold them with Small, Medium, or Large sizing – or simply a neck size.

If you’ve ever tried shopping for mid-century vintage clothing, you’ve probably run into shirts simply with numeric dimensions, and at the time, that’s how most men’s garments were sold.

Materials, too, emphasize the shirt’s leisure or vacation aura. Aside from cotton or linen, more common with guayaberas, gabardine, a soft, drape-like twilled wool, and rayon made the wider, looser cut feel practically effortless. As the style became more common, clothing brands maintained the same silhouette and feel but switched over to polyester.

Cuban Collar by Mango

Modern Cuban Shirt Revival

It wasn’t until 2014 that the Cuban collar shirt returned as a menswear essential, but its rise wasn’t as rapid. At the time, Louis Vuitton and Missoni snuck it in for a hint of Americana amongst loose-fitting casual staples like unstructured blazers, knee-length shorts, and knitwear.

If you weren’t actively looking for it, you likely missed it. Yet, in the four years since, the shirts’ boxy shape and double-notch collar remain a staple as menswear presentations become more casual, eschewing more traditional suiting for streetwear- and even workwear-influenced pieces.

Cuban collar Reiss

How to Wear a Cuban Collar Shirt

There’s plenty of vintage inspiration out there, if you want to dabble with classic Americana. However, for everyday wear, you’ve got to think about contrasts – or, more specifically, the right degree of them. 

For instance, a Cuban collar shirt with ultra-skinny jeans winds up seeming too draped – as if you’re trying out a dress and it’s too short. Conversely, its cut seems too matchy-matchy with wide-legged, structured jeans.

Rather, for pants, a slim and tapered silhouette, like a good-fitting pair of chinos, is often the way to go. Leave the shirt hanging out for a clearly casual character, or loosely tuck it in and belt the waist.

Whatever you do, always leave a bit of breathing room.

Cuban collar by Stella McCartney

Best Cuban Collar Shirts for Men

In modern times, too, we’re not left with solid colors or, as you’ve seen in many vintage listings, western-style embroidery. Beyond, lookbooks and Fashion Week presentations indicate almost everything is possible. 

Try the shirt with a floral print, stripes, or an updated Hawaiian pattern. Go light with cotton, or reference the ‘50s with a silk-like material. And, as casual suits come back in style, this silhouette – with the collar worn over the blazer’s lapels – makes an easy-going, classic complement.

Cuban collar by Ziran

1. Classic Cool

A classic take on the Cuban collar never goes out of style. Look for traditional colors and themes that look like they're lifted from a 1950s holiday vacation ad. Simple cropped black pants and sockless look give it a relaxed summer feel without competing with the shirt.

Cuban collar by Reiss

2. Summer Stripes

Another menswear classic which is getting a revival is vertical stripes. It's a flattering pattern for all body types (unlike horizontal stripes) — look for classic colors  and you'll have a summer wardrobe staple.

Cuban collar by Todd Snyder

3. Modern Florals

While florals are a classic print on Cuban collar shirts, look for modern takes on the classic illustrations that reference the past but also edge forward.

Cuban Collar by KOOVS

4. Modern Tropical Photographic Print

Another modern twist on the traditional Cuban collar shirt is the use of  photographic prints. Through recent technology, photo-like images can be printed onto fabric which can give an entirely contemporary feel.