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.

Weekend Workhorse

Where the Henley shirt really excels is as a piece of off-duty attire. Its casual versatility means it can be mixed and matched with almost anything in your casual wardrobe. Plus, the added neck detail makes it look more considered than just a simple T-shirt.

For a foolproof weekend look, start with a pair of white canvas sneakers. Next, opt for slim-fit selvedge denim and layer a grey or white Henley beneath a block-colour overshirt.

The Best Brands For Henley Shirts

Orlebar Brown

When it comes to resort-wear, there are few brands that pack a more stylish punch than Orlebar Brown. The British brand is best known for its premium, tailored swim shorts, but its breezy Henley shirts are every bit as beach-friendly.

Buy Now: £95.00

H&M

The Henley shirt is nothing if not a stripped-back, casual classic. Coincidentally, that sort of thing just so happens to be high-street giant H&M’s forte. Expect simple styling, contemporary cuts and prices that’ll leave you with plenty of change.

Buy Now: £8.99

James Perse

Few brands know their way around a T-shirt better than LA’s James Perse. Since 1994, the label has been crafting premium tees and beyond, with a focus on relaxed styling. Check out the brand’s made-in-Japan Henleys for some solid, premium options.

Buy Now: £145.00

Polo Ralph Lauren

For preppy, East Coast style, few brands are better equipped to deliver the goods than New York’s Ralph Lauren. Better still, RL was the first label to take the Henley global, so it makes sense to buy from the originator.

Buy Now: £80.00

Club Monaco

Club Monaco is actually owned by Henley masters Ralph Lauren, so you can expect a similar attention to detail here as the parent company. The brand is more well known for its considered basics though, rather than all-out preppy-ness, so expect to be able to walk in store, close your eyes and easily pick out a stylish outfit that works from head to toe.

Buy Now: £130.00

Sunspel

If budget isn’t an issue, you might want to consider Sunspel. The British brand is known for its luxury take on the essentials, offering premium fabrication and superior attention to detail. Oh, and excellent fits as standard, of course.

Buy Now: £75.00

Outerknown

Sustainability is the biggest word in fashion at the moment. It’s also something that’s central to everything Outerknown does. Founded by surfing legend Kelly Slater, the label’s offerings are heavy on the laid-back styling with beach appeal aplenty. Couple that with a commitment to ethical and environmentally sound production and you’ve got gear you can rock totally guilt-free.

Buy Now: £67.00

J.Crew

American favourite J.Crew is all about the simple things done well. Classic pieces are given a modern spin, resulting in a range of stylish essentials you can keep reaching for year after year. Keep an eye out for the label’s signature garment-dyed pieces for a relaxed, worn-in look.

Buy Now: £50.00

Hugo Boss

Hugo Boss may be more well known for its tailoring, which is often sported by brand ambassador Chris Hemsworth, but the German giant is a dab hand at casual dress too. Its Henleys are well-made and come in a range of wearable colours, making them easy to pair with jeans, chinos or shorts come summer.

Buy Now: £59.00

Jigsaw

For quality clothing with interesting details and affordable prices, you can’t go wrong with Jigsaw. It’s one of the high street’s best kept menswear secrets and its henley shirts are more than worthy of inclusion in this list. Expect simple designs that are made to last.

Buy Now: £41.00