As one of the most iconic pieces of clothing of the 20th century, this retro button-down has made a huge comeback. Whether you’re on vacation in the tropics or heading to lunch with friends, this guide will show you how to rock a Cuban collar shirt to perfection.
History of the Cuban Collar Shirt
The history of the Cuban collar shirt dates back to the 18th century in South America, and it entered the mainstream market by the early 1900s. Initially serving as a uniform for working-class men, it took the world by storm in the ’50s, becoming a staple of every gent’s wardrobe. From a suburban dad to Elvis Presley, the Cuban collar is one of the most versatile shirts in the contemporary history of menswear.
Cuban Collar Shirt Outfits
Shirt with Trousers
During the transitional months, keep yourself cool and warm at the same time in a Cuban collar shirt and trousers. Opt for dark-colored trousers for colder months, or embrace the warmer weather in white pants. To complete the look, tuck the Cuban collar shirt into your bottom half and pinroll your pants. You can rock this look at a festival, casual work function, or summer holiday – have some fun and express yourself creatively.
Shirt with Suit
Put a funky spin on your traditional suit by adding a Cuban collar shirt. Choose a suit in earth tones like beige or stone and pair it with a contrasting shirt. Keep the jacket unbuttoned for a relaxed vibe when attending semi-formal or cocktail events.
Shirt with Shorts
Embrace the sunny days by showing off your legs. Opt for monochromatic tones when pairing your Cuban collar shirt with shorts. Continue the laidback theme with sneakers or sandals, and you’ll be comfortable and stylish throughout the day.
Shirt with Jeans
Take yourself back to the ’70s with a Cuban collar shirt and jeans. From a tight-fitting shirt with bell bottoms to an oversized printed button-down paired with blue denim, there are many ways to style this look. If you’re a fan of Canadian tuxedos, why not rock double denim?
Shirt with T-shirt
Take a leaf out of the vintage book by complementing the Cuban collar shirt with a T-shirt. As a staple to the ’50s wardrobes, white T-shirts look best with bright colors, so don’t be afraid to experiment a bit. Complete the look with cutoff shorts and sneakers or chinos and loafers.
Shirt and Matching Bottoms
Dress stylishly without much effort by wearing a matching outfit. Choose from long, mid, or short-sleeved shirts and find bottoms that match. Whether it be patterned, the same color, or from a similar set, this is a statement ensemble for a confident man. Mix things up by rocking shorts instead of trousers, and complete the look with a pair of sneakers – this is a funky getup that stands out.
How to Wear a Cuban Collar Shirt
- Experiment with modern and traditional variants to see which ones work best for you.
- The transition between seasons by wearing a long-sleeved Cuban collar shirt.
- Stick to lighter materials to keep that warm-weather outlook as a unifying thread.
- Tuck the shirt into your pants and wear it under an unstructured blazer.
- Experiment with colors and designs, no matter the season.
Cuban Collar Outfits FAQs
What is a Cuban collar shirt?
You can recognize a Cuban collar shirt from its open, lapel-like collar, loose, boxy cut, and short sleeves. Cuban collar shirts are usually made from lightweight material and the silhouette may remind you of a bowling shirt.
How do you style a Cuban collar shirt?
Because of their lightweight and loose feel, Cuban collar shirts are ideal for the warmer months – especially relaxed occasions like holidays and festivals. They are a versatile piece that can be worn with jeans, shorts, and even under a light-colored suit for a summer cocktail party. Because Cuban collar shirts are generally loose-fitting, some men choose to tuck it in and then pinroll their trousers for a more fitted and less casual look.
Where can I buy Cuban collar shirts?
Cuban collar shirts are available at every price point, from online fast-fashion destinations like ASOS to designer boutiques. Another option is to go authentic and purchase a Cuban collar shirt from a vintage store. These shirts will have unique patterns that will make your outfit stand out.
Alexandra Feiam is an experienced fashion writer who holds a degree in journalism. She has an impressive portfolio and expertise working as the Editor at Power Retail and Commercial Content Editor at Newscorp. Ally has been writing for The TrendSpotter since 2018, and her work has been featured in notable publications such as The Herald Sun, Arirang TV South Korea, Kidspot, The House of Wellness, and The Daily Telegraph.
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