Men’s Henley shirts. How and when to wear them

Henley shirts for outdoor activities
Image by Outdoor

Consider the Henley.

It’s not a t-shirt. Nor is it a button-up shirt. It’s sort of in between. It’s not a polo shirt. Rather, it’s sort of like a polo shirt with the collar cut off. It’s not certainly not formal attire. But it’s probably not appropriate for casual office attire either.

Consider this about the Henley too: a Henley is often quite good-looking and stylish. That’s a bit surprising, actually, given that Henley’s are closely related to the least-attractive item of men’s clothing in history: those one-piece, romper-like items of underwear called the  Union suit .

Consider this as well about Henleys: They look good on many guys, particularly those who are toned and fit. (That’s not surprising given that the Henley shirt was traditionally worn by British rowers in the 1800s.)

Henley’s are also comfortable, available in a variety of colors, and can be dressed up a bit by choosing pants or a jacket wisely.

In other words, the Henley is an unusual shirt. But you should probably wear one from time to time. Particularly on the weekends and particularly if you’ve put in the effort to be in shape.

Henley Shirts originated from British rowers
Image by Heddels

The Henley: a shirt for all season

“I really like a Henley,” says Joanna Medeiros, a stylist with Taelor. “They're very, very versatile.

In warm weather in the most casual of environments (walking the dog, brunch at a laid-back restaurant, etc.), Henleys can be worn on their own.

“Or you can layer them. Especially during the winter,” Joanna says. “They can be worn underneath a suit jacket to dress it up a bit. Or pair a Henley with jeans and you can kind of dress it down that way.”

Short sleeves Henley shirt
Image by Allure&Co.

The classic Henley comes with three buttons. Although you will occasionally see Henleys with as many as five. But no matter how many buttons there are, you’re free to do with them what you like, Joanna says.

“You can button them all. Or unbutton the top one,” Joanna says, noting that it’s even OK to unbutton them all, although many guys aren’t comfortable doing so and exposing their chest hair.

Henleys go with just about everything

Henleys are the utility player of men’s wear.

You can put almost any type of casual outerwear on top of a Henley and look stylish. Jean jackets, suit jackets, hoodies, etc. all work well with Henleys. And if the weather is a bit chilly, a Henley pairs particularly well with a bomber jacket , according to Melissa Slavick, another Taelor stylist.

You can also wear just about any bottom with a Henley. Jeans add a rugged and casual dimension. Chinos dress up Henleys a bit. 

The right fit for a Henley

Now unless you’re particularly lucky and/or have worked particularly hard, you probably don’t have the physique of a British oarsman from the 1800s. That doesn’t mean you can’t wear a Henley. It just means you need to pay particular attention to which Henley you wear.

As always, the key is to wear something that fits. So take the time to learn your measurements .

Once you know your numbers, choose a Henley that fits your chest snuggly, but not skin tight. A Henley isn’t performance wear. They are usually made of cotton or wool, so you’ll need a bit of room to maintain comfort and to keep from getting too sweaty.

Henley and jeans
Image by Millennial Magazine

If you’re the sort who likes to wear a t-shirt under a Henley for additional warmth during the colder months, make sure the Henley is big enough in the chest to accommodate it. 

Henley’s come in both short- and long-sleeve versions. The key to looking good in either version is to know your bicep size and pick a Henley that fits your arm snuggly.

Finally, a Henley can be forgiving on a less-than-svelte physique. So avoid the urge to hide any surplus weight under an oversized Henley. You’ll look better by far if you choose a Henley that fits well, albeit not too tightly, across the midsection.

Of course the easiest way to choose a Henley that works for you is to become a Taelor customer. Taelor is a menswear rental subscription service dedicated to helping men look their best when it matters most. Our styling service, powered by a human stylist and assisted by artificial intelligence, finds the clothes that help you win – at work, on a date, at a party, or wherever you plan to spend time. When you join Taelor, your personal stylist can help you select colors and sizes of Henleys – and just about any other item of menswear – that are ideal for you and your body type.


Rent Henley Shirts from Taelor

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