What Season Do You Wear Henley Shirts?

Henley Shirts

If you’re a man looking to elevate your style, one of the best clothing items you can have is a henley shirt. These shirts are a huge step above your typical tees but aren’t as complicated as dress shirts, polos, or Cuban shirts.

On top of that, henleys are known for being very comfortable. They were originally designed as rowing shirts, so they allow a lot of movement, have a breathable fabric and feel very nice on the skin.

But when you buy your first henley shirt, you might wonder which season is the best time to wear one. After all, there are many clothing items designed for specific seasons, and you don’t want to make the mistake of wearing a henley at the wrong time.

So, in this article, we’ll look at the best season to wear a henley shirt and a couple of cool ways to style a henley, depending on the season. That way, you’ll be dressing as sharp as ever in your new henleys, regardless of the time of the year.

Let’s get into it. 

When Is the Best Time to Wear a Henley Shirt?

One of the best things about henleys is their flexibility. Since they come in both long and short-sleeved varieties, you can wear them at any time, regardless of the season. In fact, we’ve seen people rock henley shirts in winter, spring, summer, and fall.

These are some of the most versatile shirts you will ever own. Not only are they appropriate for all seasons, but they work with many outfits as well. Henleys are typically known as the ultimate casual shirt that you can always wear with jeans and boots to look sharp.

However, you can even dress a henley up and wear it with formal outfits. For example, you can wear a black henley with a suit in place of a dress shirt for a more modern look. Or, you can wear a henley with chinos and a nice vest for a more vintage take on the shirt.

That said, you still have to choose the right henley for the season.

For example, if you want to wear a henley shirt during the colder seasons, you may want to get one with long sleeves and made of a warmer material. That way, the henley serves as a great base layer for your outfit that still keeps you warm.

But if you want to wear one in the summer, you might want to stick to the lightweight short-sleeved options. At the end of the day, you want to make sure that the henley you’re wearing doesn’t just look good but also feels comfortable.

Styling a Henley Shirt for Different Seasons

Henleys are all-season clothing. You don’t have to worry about the time of the year when putting one of these on. However, you have to ensure that you have the right outfit to match the weather. That way, you still look dressed for the season, feel comfortable, and get to wear your favorite henley shirts!

So, here are a couple of different ways to style a henley shirt, depending on the season.

Cold Seasons

As mentioned earlier, if you want to wear one in the winter or when the temperatures start to drop, it’s best to get a warmer long-sleeved henley. When you have one of these in your closet, you’ll have a great shirt to wear in the winter with just about any outfit you have.

Our favorite way to wear a henley shirt in the winter is with a nice winter suit. We really like the way henleys look when you swap them out for a dress shirt when wearing a suit. This could be a solid-colored or a patterned suit, as henleys easily work with either. Because the buttons on a henley mirror the buttons on a dress shirt, it easily works with a suit. To make it fit the season even more, you can add a scarf and even a hat to the outfit.

When wearing a henley casually in the winter, we like using them as base layers. For example, one of our go-to ways to wear a henley in the winter is under a flannel. Henleys bridge the gap between formal and casual shirts, so they blend really well when you wear them under a flannel.

Warm Seasons

When things start to heat up, you won’t be able to wear henleys as you did in the winter or fall. This is because you want to keep cool during the summer and spring months, and luckily henleys allow you to do that as well.

You can opt for either long or short-sleeved henleys during the warmer months as long as it’s made out of a lightweight and breathable material. From there, you can’t go wrong by wearing a henley with a nice pair of jeans and sneakers. This is a slightly more elevated take on the jeans and t-shirt outfit and is one that will stand the test of time.

Another cool way we’ve seen people wearing henleys recently is with shorts. While this isn’t the most traditional way to wear a henley, the way these shirts are cut allows them to work really well with shorts. You can either finish this outfit with sneakers or even espadrilles to complete the casual look.

And just like with your winter suits, you can use a henley with your summer suits as well. You might want to dress a bit lighter when the sun starts to get a bit hotter, but rest assured that your henley will look great in a summer suit. 


If you’re looking for a nice shirt that you can wear every day that elevates your style, the henley is a great option. 

The reason these are such popular shirts is that they aren’t for one specific season. You can use henleys to elevate your outfits any time of the year as these are some of the most versatile and flexible shirts you can have in your wardrobe!