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How to style the henley shirt, the versatile men’s fashion item your wardrobe needs

Pick up these underrated heroes of the closet

Man in sunglasses and henley
KC Stone / The Manual

Men have a small amount of choices when it comes to shirts—dress shirt, polo, sweater, t-shirt that seems like all there is. Of course, that is only if you don’t dive into all of the diamonds in the rough. There are a lot of unsung heroes in the closet that you have likely been overlooking. The henley shirt is the number one most underrated and often overlooked shirt in men’s fashion. There are so many uses for it that men tend to forget about.

It may have started as the top portion of long underwear, but the knit shirt with two or more buttons at the opening became one of the most coveted uniform shirts due to its comfort and versatility. It became so beloved that the name henley came from its use as the uniform during the annual Henley Royal Regatta, one of the first organized rowing events in British history. Ever since, it has been a mainstay in our wardrobes, but now it’s time that we all learn how to wear these in ways that get the full potential out of the henley.

Man in green henley and PF Flyers
KC Stone / The Manual

Keep it casual

The first and most basic way to wear a henley shirt is to keep it on the casual side. With its origins as long underwear and as a sports uniform top, it makes sense that it would lend itself well to the casual outfit. Pairing it with a pair of jeans and sneakers is the ultimate in casual wear, perfect for running errands or catching a movie.

Steal the look

Henley – This look from Abercrombie and Fitch is a few years old, so you’ll have to go with something a little more updated, like this option from True Classic.

Jeans – DU/ER Performance Slim is a great option for your basic black jeans. As a true black, the color is as rich as it is black.

Shoes – P.F. Flyers Deep Olive Hi Top is the perfect way to stand out with a classic shoe with a color twist.

Sunglasses – Rheos Stono in Olive is the perfect way to tie in all the green in a subtle way. These glasses are made for those who love the water, so keep them on when you change for the beach.

Watch – The Armitron Metro is one of the most striking new drops of the year. This year, old is the new…well, new. And this feels like the perfect throwback to give this outfit a little personality.

Man in linen suit with henley and hat
KC Stone / The Manual

Dress it up

Here is the trick for getting creative with a henley: Treat it like you would a sweater. If you would wear a sweater with an outfit, swap it out for a sweater and see how that looks. In this situation, wearing a linen suit already feels a little more casual, so throwing on a pair of drivers and an elevated short-sleeve henley is a great way to get creative.

Steal the look

Suit – The Dandy Del Mar Brisa Sedona set is the absolutely perfect suit for the upcoming season. The striking color doubles down on that old-is-new theme for 2024, and the linen will serve you quite well over the summer months.

HenleyY.Chroma is designed to help you put some color in your wardrobe. Everything they make is about standing out, and that goes the same even for their white short-sleeved henley.

Pocket Square – Cad and The Dandy knows how to make you stand out as well. This outfit is all about standing out, and therefore, this pocket square has to do the same.

Shoes – While you are standing out, you might as well get the best of the best. Bruno Magli will always fit the best and look the best. That makes these Bruno Magli Xane Casual Suede Slip-Ons the perfect choice.

Hat – If you really want to stand out, then stand out with a great hat as an addition to this already stellar look. This Southern Gents Trilby will get you all the compliments.

Man in jeans and flannel with henly under it
KC Stone / The Manual

It’s a base layer

At its most basic, the henley is the perfect base layer. It is functional in keeping you warm while being thin enough to go under your shirts. This is the most rugged look of any other with the henley and can be seen as Tom Cruise’s go-to look in the film Jack Reacher. It is a great way to stack colors and give your looks depth.

Steal the look

Shirt – Snaps Clothing has a way of taking the most rugged looks and making them feel elevated. And this flannel by Snaps is one of the best they have in their colorways.

Henley – The DEVIL DOG DUNGAREES Indigo Slub Henley is a rich blue and classic silhouette that represents everything the company stands for. It is rugged, attractive, and comfortable. Just like everything else in their collection.

Jeans – Speaking of D3, the same company that makes the henley is the one that makes the selvage jeans that keep looking rugged. These jeans are some of the best in the world and will look better than any other. These specific jeans are limited to the 75th anniversary and sold out, but there is a long list in this collection that works just as well.

Shoes – Wolverine was there at the beginning of the work boot. 140 years later, they released the anniversary of the boot, and they are the perfect boot to keep the look rugged and stylish at the same time.

Glasses – Wiley X has spent the last four decades making the best protective eyewear on the market. Started by an Army veteran, they are made by people who know what is needed from glasses. These WX Founder are the glasses that look as rugged as they feel. The robust build and removable side shields make them ideal for outdoor adventures or casual everyday wear.

Man in purple henley and chinos
KC Stone / The Manual

It is the feature

The henley isn’t simply a layering piece. They are also made to be the feature of an outfit. The best henleys to feature are the ones dyed with the brightest colors. Making a unique henley, like this purple one from Banana Republic, is the easiest shirt to center an entire outfit around.

Steal the look

Henley – The Banana Republic henley is long discontinued, but a good replacement is the UNTUCKit Textured Henley. The vibrant purple is easy to make the centerpiece of any outfit.

Pants – The Hockerty Prince of Whales Limited Edition Tweed pants are anything but basic. Not only will they look great with virtually any outfit, but they will make you feel like you’re dressed for the Peaky Blinders set every day.

Shoes – Kizik Lavender Prague is a purple shoe. There isn’t much more to be said about them. While Kizik has dozens of great shoes in unique styles and colors, there is something to be said about a man who can wear a pair of lavender shoes.

Watch – We’ve got a bit of an obsession with a good field watch. They can be worn through the toughest and harshest environments. The 5.11 Outpost Chrono in gray is the most versatile field watch you’ll have in your collection.

Man in long coat and black henley
KC Stone / The Manual

It’s a top layer

Remember when we said to wear the henley like a sweater? Wearing the usual base layer or former underwear as a top layer is a fun and unique way to utilize the layering ability of the henley shirt. Layering it over the top of a dress shirt and under a suit coat or overcoat makes it the same as a sweater, with a little twist showing off the buttons.

Steal the look

Henley – DEVIL DOG DUNGAREES strikes again with this black henley that can be worn as a base layer but is soft and luxurious enough to take the place of your sweaters.

Dress shirt – Suit Shop is one of the few companies that can make the impossible (shopping for a suit online) feel like ordering a pizza. With their comprehensive sizing guide, they tell you exactly what to get. And everything from a suit to this simple white dress shirt looks great.

Pants – Men have been going to Men’s Wearhouse for their suiting needs for what feels like forever. While suit snobs may turn up their noses at the king of the off-the-rack, they hit their stride with the Joseph Abboud made-to-measure…these pants are a testament to the quality of the work.

Overcoat – Lululemon is best known for workout clothing. But this overcoat is the newest version of the trench coat. It looks nothing like Humphrey Bogart’s, but it may do the impossible and look even better.

If you ever start to feel a little bored with the wardrobe in your closet, reach for a henley and inject some new life into your ensembles.

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Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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