Cuban collar shirt

5 Ways to Wear a Cuban Collar Shirt This Winter

The Cuban collar shirt is a timeless and stylish piece that transcends seasons. Originally associated with laid-back beach vacations, this shirt has evolved into a chic, versatile option for various occasions. While traditionally seen in summer wardrobes, the Cuban collar shirt can be effortlessly integrated into your winter style. Whether layered, styled with smart trousers, or paired with cozy outerwear, a Cuban collar shirt can elevate your winter wardrobe in unexpected ways.

In this blog, we’ll explore five fashionable ways to wear a Cuban collar shirt this winter. Embrace the chic, laid-back vibe of the Cuban collar and make it work for the colder months.

1. Layer It Under a Wool Blazer for a Smart-Casual Look

A wool blazer is a must-have in any winter wardrobe, but how do you add a twist to a classic? The answer is simple: layer your Cuban collar shirt under a sleek wool blazer. This combination creates a smart-casual look that stands out from the typical button-down shirt.

The Cuban collar shirt’s relaxed design contrasts perfectly with the structured blazer, making the look feel modern and fresh. Opt for a neutral or dark-colored Cuban collar shirt to keep the ensemble grounded during the colder months. Pair the outfit with chinos or tailored trousers for a polished yet effortlessly stylish appearance.

Styling Tip: For a more polished vibe, choose a Cuban collar shirt in a luxurious fabric like silk or fine cotton. These materials will not only add texture to your look but also offer a bit of extra warmth.

2. Pair It with a Cozy Knit Sweater for Extra Warmth

One of the simplest ways to wear a Cuban collar shirt in winter is by layering it under a chunky knit sweater. A Cuban collar shirt adds a touch of refinement, while the sweater provides the essential warmth needed for the colder months.

This layered look is both stylish and practical. The open collar of the Cuban shirt peeking from under the sweater creates a layered, cozy aesthetic that feels casual yet thoughtful. You can experiment with different textures, such as pairing a linen Cuban collar shirt with a wool sweater or a cotton shirt with a cashmere knit.

Styling Tip: Opt for a monochrome color palette for a minimalist look or mix contrasting textures to add depth to your outfit. The Cuban collar shirt can peek out from a crew neck or turtleneck sweater for added flair.

3. Layer It with a Puffer Jacket for a Trendy Street Style

Puffer jackets are a winter wardrobe staple that can look just as stylish as they are warm. For an on-trend street style look, try layering your Cuban collar shirt underneath a puffer jacket. The relaxed, boxy fit of the Cuban collar shirt pairs well with the oversized silhouette of a puffer jacket, creating a balanced and effortless look.

Choose a Cuban collar shirt in a solid color to maintain the sleek, urban feel or go for a printed Cuban collar shirt to add more personality to your outfit. The combination of the casual Cuban shirt and the structured puffer jacket creates an intriguing contrast that is both comfortable and fashionable.

Styling Tip: For a laid-back yet chic winter outfit, pair your Cuban collar shirt and puffer jacket with jeans or joggers. Finish the look with a pair of sneakers for a comfortable and stylish ensemble.

4. Style It with Leather Pants for a Bold, Edgy Look

If you’re aiming for a bolder winter outfit, pairing a Cuban collar shirt with leather pants is a surefire way to turn heads. The sleek, edgy vibe of leather pants contrasts with the relaxed, retro flair of the Cuban collar shirt, creating a unique and attention-grabbing ensemble.


For colder days, layer the Cuban collar shirt under a leather jacket or a long wool coat to ensure warmth. This combination is perfect for winter nights out, as the leather elements add sophistication and an undeniable cool factor.

Styling Tip: Go for a fitted Cuban collar shirt to balance the boldness of the leather pants. Add a pair of ankle boots or combat boots to complete the edgy vibe.

5. Tuck It Into High-Waisted Pants for a Sophisticated Touch

If you're looking for a sophisticated way to wear a Cuban collar shirt during the winter, tucking it into high-waisted trousers is a smart choice. High-waisted pants elongate the legs and give a sleek, tailored look. The printed cuban collar shirt adds a relaxed, chic touch to the outfit without compromising on elegance.

You can opt for wool or tweed trousers for added winter warmth or experiment with wide-legged pants for a more contemporary look. This styling choice strikes the perfect balance between polished and relaxed, making it a great option for both workdays and weekends.

Styling Tip: Add a belt to accentuate the high-waisted style and create a more defined silhouette. A statement belt can also be used to add a touch of personality to your Cuban collar shirt look.

FAQs 

1. Can I wear a Cuban collar shirt to a formal event in winter?

Yes, you can! To make the Cuban collar shirt appropriate for formal events, layer it under a tailored jacket or wool blazer. Choose darker shades or subtle patterns for a sophisticated appearance. Pair it with dress trousers or chinos to complete the look.

2. How do I keep warm while wearing a Cuban collar shirt in winter?

Layering is key to staying warm while wearing a Cuban collar shirt in winter. Pair it with thicker fabrics like wool or cashmere and layer it under jackets, knit sweaters, or coats. You can also add accessories like scarves and gloves to keep the cold at bay.

3. Are Cuban collar shirts suitable for all body types?

Yes, Cuban collar shirts are generally flattering for all body types. The relaxed cut offers comfort and allows for ease of movement. However, choosing a Cuban collar shirt that fits well in the shoulders and chest will ensure that it looks sharp and tailored.

4. Can I wear a Cuban collar shirt with jeans in winter?

Absolutely! Pairing a Cuban collar shirt with jeans is a great way to keep things casual yet stylish. For winter, opt for darker, thicker denim, or even corduroy jeans. Layering with a cozy sweater or jacket will keep you warm while still looking chic.

5. What colors work best for Cuban collar shirts in winter?

For winter, darker, neutral shades like black, navy, or deep greens work well. You can also incorporate rich jewel tones or muted pastels for a stylish yet understated look. The key is to choose colors that blend seamlessly with your winter wardrobe, allowing the Cuban collar shirt to shine as a versatile piece.

The casual shirts for men is an unexpectedly versatile piece that can be styled for winter. Whether layered under a wool blazer, worn with leather pants, or tucked into high-waisted trousers, this shirt adds a relaxed yet sophisticated touch to any winter ensemble. Its laid-back design pairs perfectly with warmer layers and outerwear, making it a stylish choice for colder months. Embrace the Cuban collar shirt in your winter wardrobe to add a chic, retro flair that’s both fashionable and functional.

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