Men's Henley Shirts - The Ultimate Guide

I have a love/hate relationship with Henleys, but that doesn't mean you should avoid them.

Rugged, durable, and suitable for wearing as a layering piece or on their own, I love them when they're worn properly and on the right body type.


A lot of men crap the bed when wearing Henleys. When done right, they'll look sexy and stylish. When not... oouuuf.

What is a Henley shirt?

A men's Henley shirt is a type of casual shirt that typically has a round neckline with a buttoned placket, similar to a polo shirt.

It is typically made of comfortable and breathable fabrics and it can be either short-sleeved or long-sleeved.

It's known for its versatility and can be worn as a standalone shirt or layered under jackets or sweaters. 

Why is it called a 'Henley' shirt?

This shirt is named after the town of Henley-on-Thames in Oxfordshire, England.

Originally worn by the participants in the Henley Royal Regatta, it gained popularity among rowers and eventually became a fashionable item of clothing worn by both men and women. 

Are Henley shirts suitable for different body types?

No! Learn more in my 'Who Can Wear Henley Shirts?' section below.

Can men wear Henley shirts for dressier occasions?

Also, no! Henleys are a casual item only. 

What are the different styles and variations of men's Henley shirts?

The classic Henley shirt typically features a round neckline with a button-up placket, long sleeves, and a straight or slightly curved hemline. However, there are also short-sleeved Henley shirts available for warmer weather.

In terms of variations, you can find Henley shirts in various fabrics such as cotton, linen, or even blends with synthetic materials.

How do I layer a Henley shirt?

Like your t-shirts, I think that a Henley should be worn as your base layer, if you're in good shape, it will highlight your physical attributes. That said you could wear it over an undershirt or thin t-shirt, provided that you can't see the the outline underneath the Henley.

I personally think that a Henley looks best by itself, but you could always wear it under a jacket or an overshirt if you want some extra insulation.

Henley Shirts Mistakes Most Men Make

Despite its relatively plain aesthetic, the Henley shirt can be tricky to pull off. Here are the most common mistakes you want to avoid:

  • Wearing Henleys with bold colors or loud patterns.
    These never look good. If in doubt, stick to dark neutral shades, as these are the most versatile and stylish options.

  • Wearing for non-casual dress codes.
    Henleys are casual shirts and work only in casual outfits.

  • Wearing a Henley if you don't have the body for it.
    This is a big no-no. Learn more in my 'Who Can Wear Henley Shirts?' section below.

Want to see all the mistakes to avoid specifically for your age, height, body type, and skin tone? Check out my Essential Capsule Wardrobe App.


Like your sweaters and t-shirts, I'd recommend sticking with neutral-colored Henley unless you really know what you're doing.

Some of my favorite shades are black, navy, and charcoal.


Generally, Henleys will be made out of cotton, so there’s really not much choice outside of that, but you still need to consider fabric weights depending on the time of year.

The main thing to know is that lighter weights should be worn in warm weather. Thicker, heavier fabrics in cooler weather.

You can get them in everything from a lightweight summer weave, where it feels like a t-shirt, to thicker, quilted versions which will keep you warm during the cooler months.

You don’t have to worry too much when buying them because, based on the time of year, most brands will carry the appropriate weights. But I still want you to be aware of it just in case.

Different Types Of Henley Shirts

Short-Sleeve Henleys

A short-sleeve Henley is similar to a polo shirt but it hasn't got a collar and it usually has a more relaxed fit.

Wear your short-sleeve Henley as you would a crewneck t-shirt. The two are interchangeable in the same outfits and can be worn on their own or underneath a jacket.

Long-Sleeve Henleys

In my opinion, long-sleeve Henleys look better than short-sleeve ones and they're a great go-to item when you're looking for something between a polo or a crewneck t-shirt and a sweater. 

During the warmer months you can wear them with the sleeves pushed up. Trust me, women love to see sleeves rolled/pushed up around your forearms.

However, I mentioned earlier that Henleys aren’t for everyone...

Who Can Wear Henley Shirts?

Whether you can wear a Henley or not depends solely on your body type, and I hate to say it, but not everyone can wear one.

Slim Build

If you’re a thin guy, no matter your height, if you want to wear a Henley, you need to nail the fit, especially if you’re going to wear a long-sleeved version. If the fit is too loose, it’ll make you look thinner and more frail than you are – not good!

A long-sleeve Henleys on thinner men if they’re layered underneath a jacket, like the below-right image. When worn on their own, it really spotlights and elongates your thinner torso, slimmer arms and neck, like the image on the left. So if you’re a thinner guy and want to wear a Henley on its own, then wear a short sleeve version since it’ll look similar to a t-shirt.

Athletic Build

I personally think that Henleys look best when worn by guys with a muscular athletic build. Exhibit A:

The reason why is that the Henley was originally designed as an under-layer rather than an outer one. As a result, they have a really trim fit across your body, particularly throughout your shoulders and arms which can look really sexy if you’re in shape but...

Larger Build

If you’re a rotund gentleman (aka you’ have a belly - this includes dad-bods), you shouldn't wear a Henley shirt, period.

Allow me to show you why and explain. See Exhibit B:

Because of the button placket on the front, coupled with the lack of a collar, a Henley will shine a massive spotlight on your bigger torso.

This is when a polo shirt is perfect and should be used instead because a polo shirt’s collar will visually keep your torso balanced and in proportion, so your top half doesn’t look so big compared to your bottom half. The image below of James Corden shows a guy with the exact same body type as the image above but in a polo shirt. Talk about a night and day difference…

If you want to learn more about which items will and won't work for your specific body type, check out my Essential Capsule Wardrobe app.

How To Wear A Henley Shirt

Like all your clothing, including Henleys, they should have a trim fit throughout the body and arms – no matter your body type. You never want it to be too loose anywhere because that’s when you’ll look sloppy and not put together. You shouldn’t be able to pinch more than 1-2 inches of fabric on one side of your belly button and no more than an inch around the bicep.

The image below highlights the proper fit around the torso and sleeves.

Luckily for you, I made a video on this very subject:

Outfit Ideas

Like I've already said (multiple times), the Henley should be thought of as a casual item and worn in certain ways, depending on your body type (or not at all).

Here are a few of my favorite ways to wear a henley shirt.

Charcoal Henley Shirt
Sand Chinos
White Low-Top Sneakers

As Mr. Reynolds has an athletic/muscular physique, he can get away with wearing his henley on its own.

Want to see more ways that you can wear the items in your wardrobe? Or better yet, build a complete capsule wardrobe that works specifically for your age, height, body type and skintone? Check out my Essential Capsule Wardrobe App.

Olive Work Shirt
Gray Henley
Medium Wash Jeans
White Low-Top Sneakers

Henleys work great as a layering piece during colder months and here we have one layered under a stylish olive work shirt.

Black Bomber Jacket
Charcoal Henley
Dark-Wash Jeans
Black Chukka Boots

In case you haven't guessed by now, charcoal is a super versatile color for Henley shirts. See how we've layered it under the bomber and tucked it into the front of our jeans to show off our belt and earn some bonus style points.

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