The Henley shirt might just be one of the most underrated garments in menswear. Essentially a collarless polo, legend has it that this T-shirt alternative got its big break when a Ralph Lauren buyer happened upon a vintage rowing top and declared it to be the next big thing.

His prediction may have been a little overzealous, but he was definitely onto something. The Henley might not have the same staple status as its cousin the polo shirt, or its uncle the crew neck tee, but it certainly deserves a place alongside them in a modern wardrobe.

The Henley borrows its name from the English town of Henley-on-Thames, and the famous regatta that has taken place there since the 1800s. Technically, its rowing heritage makes this button-up classic a piece of sportswear, but it’s contemporary wardrobe applications stretch far beyond the athletic.

Here we take a look at how to style one of menswear’s most misunderstood garments and where to shop for the best bang-to-buck ratio.

How To Wear A Henley Shirt

Henley-on-Holiday

It wasn’t designed for floating around resorts sipping pina coladas, but it might as well have been. A Henley shirt makes a trusty companion when it comes to soaking up some sun in style. Breezier than a conventional T-shirt with its open neck, but without the style stigma attached to a V-neck.

For a simple beach-to-bar look, team a white Henley with tailored swim shorts. Add in a pair of Birkenstocks and tie it all together with some tortoiseshell shades and nice even tan.

Tailoring With A Twist

The Henley-and-tailoring combo is a style move seldom practised. However, if your summer suiting options are stuck in a sartorial rut, the nonchalance of this casual classic can bring a dose of laid-back cool to proceedings.

For best results, wear a Henley with relaxed, unstructured tailoring in a light colour and with smart casual, suede footwear. Remember, this is an outfit for low-key summer weddings and informal gatherings, not something you want to rock up to a job interview in.