How To Wear A Cuban Collar Shirt

Like all the best things in menswear, the Cuban collar shirt is a must-have because it’s versatile. You could wear the same one to a summer wedding and again to the beach the following weekend.

This type of shirt is something of a comeback hero of men’s wardrobes. Also known as a revere collar or camp collar, it first came to prominence in the 1950s, but in more recent decades it was a shapeless garment synonymous with obnoxious tourists and Chandler Bing.

That changed in 2014 when labels like Louis Vuitton and Missoni brought it back, refreshed, ushering in a new way to wear crisp, cleanly-cut midcentury fashion. The style has been growing in popularity ever since.

The distinctive collar design was originally designed to be casual – there’s no top button, no starched fold and no shortage of chest on show. But opting for something other than a traditional collar also makes it a subtle dandy-ish decision, a conscious peacock’s step from the norm.

It’s worth the gamble. The best Cuban collar shirts are flattering to most body shapes. The collar broadens your upper body, while the casual style better carries prints and bold colours than lots of other shirt styles.

The seven looks below prove that not only do you need one this summer, you’ll get plenty of wear from it.

With Tailored Trousers


It was in the 1950s that Cuban collar shirts first made a stamp on western menswear. Think early Elvis, mid-century resort wear – maybe a touch of the well-dressed mobster for good measure. It’s technically a dressed-down look but, like everything else from the era, tailored nonetheless.

This is also one of those rare outfits from the past that you can wear pretty much unchanged in the present. Pick neutral colours, perhaps some piping detail on the shirt. On the legs, try some pinstripe trousers or a plain pleated style and tuck the shirt in for an elegant, unfussy way to see out warm summer evenings.

A penny loafer would be the traditional way to ground your look but if you want to update it for the 21st century, some low-key sneakers are the way to do it.

– Ian Taylor, editor-in-chief

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Over A T-Shirt


There’s a certain louche attitude to wearing your Cuban collar shirt with a T-shirt underneath. It means that you can wear yours without needing to bother with the buttons, letting the fabric simply drape down from your shoulders and all without risking a police caution.

The look works best with just a simple white tee underneath, a logo will distract from the star of the show above it, while white will complement anything and everything, but especially bold patterns.

Try tucking your tee into some slim fitting trousers or jeans to bring a variety of shape to the ‘fit, slim and fitted underneath against the open, wide and billowing Cuban collar above. The tuck will also prevent your tee from coming down below the hem of your shirt which can look messy.

A pair of throwback ’90s sneakers will play well with the style of the shirt tuck, while their casual nature befits what is essentially one of the most casual ways to wear your revere collar.

– Richard Jones, staff writer

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With A Suit


A Cuban collar worn with a suit may seem unconventional at first, but once you try it you’ll quickly realise this is a deadly combination come summertime. And not just because of the Tony Montana connotations.

Suits are difficult to wear in warm weather as they’re often too stuffy and restrictive, but the soft collar of the Cuban is the ideal antidote. It lacks the formality of a regular (inferior) shirt, but is smarter than a tee, working best in a smart-casual context.

For the suit itself, opt for something unstructured to complement the mid-century feel of the shirt, and finish off with white sneakers for a suitably laid back feel. Say hello to your little friend.

– Charlie Thomas, senior editor

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With Shorts


Pairing a T-shirt with shorts is surprisingly tricky territory. The problem lies in the fact that a fairly innocuous-looking T-shirt and shorts quickly get all holidaymaker casual when put side by side. A Cuban collar shirt, however, faces no such problems and is the ideal style to de-basic your summer look.

It goes without saying that board or cargo shorts aren’t allowed here. Instead go streamlined and channel some Riviera vibes by choosing tailored shorts which sit neatly somewhere about mid-thigh. Colour-wise, pared-back shades (such as stone, navy or black) come highly recommended. And, if you’re already past novice Cuban collar wearer status choose a patterned design; Hawaiian and Japanese prints are trending hard, as are block vertical stripes.

Then, slip on some simple white sneakers to keep things from veering too international euro playboy and you’re good to go.

– Luke Sampson, associate editor

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With Denim

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Most of the shirts worn by Christian Slater in True Romance had a Cuban collar on them. And in most scenes, his Elvis-obsessed character paired them with pair of light or mid-wash jeans. It’s a west-coast beach bum look (co-opted by Justin Bieber in recent years) that’s all-American in all the right ways: colourful, youthful and casually cool.

To wear it yourself, grab your favourite pair of ’90s jeans and team them with an equally roomy shirt. It’s a laid-back look so you have options: block colours and patterns both work, as does the addition of a tee or vest if you want it. Finish it off with another nod to the ’90s in a pair of chunky sneakers or throwback sports shoes.

– Ian Taylor, editor-in-chief

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Under A Jacket


Getting the right jacket to go with your Cuban collar shirt takes more than just slinging on whatever you’ve got hanging from your door peg. The rounded collar of a bomber jacket can sometimes jar with the pointedness of the Cuban collar you see while a denim jacket might err too far on the casual side. A workwear staple, the chore jacket, finds the right balance however, the simple yet calculated cut providing an able deputy to the Cuban collar’s commander in chief.

When it comes to colour, pluck for a tonally matching jacket as you don’t want to fight a printed shirt’s pattern with even more colour. A chore jacket’s hardwearing cotton twill will feed in nicely to a pair of crisp chinos underneath, and finish the look off with some smart Derbies or desert boots for a style that easily flits between three evergreen smart-casual fashion tribes – mid-century, workwear and preppy.

– Richard Jones, staff writer

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With Long Sleeves


Cuban collar shirts are usually short sleeved, which makes sense considering they’re most often worn in spring and summer. But, if you can find a long-sleeved example you’re in luck, as this may well be the most versatile shirting option around.

Wear it buttoned up for dinner; wide open over a tee on the weekend, or tucked in for just-acceptable playboy vibes. Go plain for a minimal, understated look or opt for print if you want to dazzle – either way you’ve won.

The long sleeve Cuban can be dressed up with ease. Think wide-legged, pleated trousers in a darker shade than the shirt, a classic pair of sunglasses to tuck into the top pocket, and lug soled penny loafers. You’ll be ready for casual Friday at the office, plus any date night that follows.

– Charlie Thomas, senior editor

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