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The Best Henley Shirts For Cool Casual Style

Name a more versatile piece of clothing than a henley shirt; go on, we dare you. This super functional design is a to-go undergarment, as it allows us to wear our heavyweight sweaters and jumpers over the top, securing incredible warmth in winter. However, lightweight short-sleeve henley shirts are perfect for summer, as they’re highly breathable and comfortable.

The henley shirt has always been a super practical staple piece, as it initially served as the uniform for sailors in the town of Henley-on-Thames. However, this undergarment went on a brief hiatus and didn’t merge into mainstream culture until the 1960s, after Ralph Lauren began designing henley style shirts into his menswear collections. Soon after its reincarnation, everyone began rocking these designs, recognised for their casual, laidback style; suitable to wear all year round.

Men’s Henley Shirt FAQs

Should I wear a shirt under a henley?

You wear a henley shirt exactly like a t-shirt, as you wear it as an undergarment while building layers on top of it. In the winter, to secure optimal warmth, definitely pair a long sleeve henley shirt with a sweater and a long coat; however, if it's warmer outside, you can wear this shirt alone as it’s breathable and light.

Why are they called 'henleys'?

Henley shirts got their name, as they were the traditional uniform of rowers in the English town of Henley-on-Thames. Soon after, it was integrated into a variety of different sportswear during the nineteenth century.

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Aside from a basic white tee, there is no undergarment more adaptable than a henley shirt. To celebrate the functionality of this classic top, we’ve carefully curated a list of brands manufacturing our favourite henley shirts. These shirts are of the finest quality and will quickly become the foundation of all your casual wear.

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