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How To Wear Cuban Heels

Cuban heels and heeled men's shoes have been around for centuries, but found new life in the 60's when the "Beatle Boot" was created for arguably the biggest rock band of all time, The Beatles. The design was a hybrid of the popular Chelsea boot, with the added height of a Cuban block heel. Since then, many footwear trends have come and gone, but the Cuban heeled shoe has always had a dedicated subculture of followers that aren't afraid to go against the grain.

So what can you wear them with? Here's some outfit inspiration to go with your favourite new shoes!


For a casual day to day look, why not pair brown or tan boots with dark wash or indigo raw denim jeans. For that vintage western inspired style, an exaggerated turn-up hem ties solidifies the look. The classic combination of a plain t-shirt & a plaid brushed cotton overshirt allows you to exude confidence without looking like you're trying too hard. Film star & cult internet style icon Shia Lebouf is the most recent celebrity to be seen donning Cuban Heeled shoes, a testament that they're here to stay.

Modern Mainstage

For a modern take on that classic rock star look, skinny black jeans (knee rips optional) look great with black or louder coloured boots. A western style shirt buttoned down to the chest or a loose fitting sleeveless t-shirt looks great under a leather biker jacket. You can accessorize with jewelry, a flowing scarf or a trilby hat. This look can be seen on celebrities like Alex Turner from The Arctic Monkeys & TV Personality Noel Fielding. 


Due to the high-quality craftsmanship synonymous with Cuban heels, they naturally look fantastic with a suit! A 3-piece slim fitting suit in black, navy or grey is an ideal outfit to make a solid impression in important meetings or business functions. For events like weddings and formal dinners, why not experiment with pattern and colour? Tartan, tweed and bright coloured suits are guaranteed to turn heads, informing your audience that you know what you want and aren't afraid to make independent choices. A button up shirt in a neutral tone or a dark coloured turtle neck seals the deal on your formal outfit.

Fancy a pair? Check out our specially dedicated category for our vast collection of men's heeled shoes & boots, including our Italian-made best selling brand Club Cubano. We also give you the option to add a 1/4 inch to the heel or add a rubber grip to the sole to improve traction! We hope you're feeling inspired, browse our range today!