The History of the Cuban Collar Shirt

By Ivan Yaskey 

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 since 2016. Through either lens, the Cuban collar shirt – also referred to as a camp, cabana, or revere collar shirt – has transformed from strictly retro wear into a wardrobe staple. And, beyond the obvious, the silhouette has a near-ubiquitous presence today, from all those on-trend Hawaiian shirts to the traditional guayabera.

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 Antony Morato

Cuban Collar Shirt by French Connection

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.

Cuban Collar by KOOVS

Cuban Collar by Mango

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. 

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 Prada

Cuban collar by Stella McCartney

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.

Cuban collar Reiss

Cuban collar by Reiss

Materials, too, emphasized 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.

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 by Reiss

Cuban collar by Todd Snyder

There’s plenty of vintage inspiration out there, either on blogs or a browse through Pinterest, 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 Ziran

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’s 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.