How To Style A Henley Shirt In Different Seasons

How To Style A Henley Shirt In Different Seasons

You don’t have to put your Henleys in the back of your closet just because winter is coming around.

How To Style A Henley Shirt In Different Seasons

If you’re looking for a shirt that you can rely on every season of the year, you won’t go wrong with a Henley. Nowadays, the Henley is a staple in most men’s wardrobes as they are comfortable, come in many colors, and can blend in with just about any outfit.

That said, wearing a Henley in the winter is very different from wearing a Henley in the summer. And if you don’t style the Henley for the season, you may end up looking out of place. So, let’s look at how you can style a Henley for every season of the year.

That way, you’ll always wear the Henley in a way that fits the season and event you’re attending!

When Is the Best Time to Wear a Henley?

You don’t have to worry about the season when wearing a Henley. These are evergreen pieces, meaning you can wear them whether winter, spring, summer, or fall. On top of that, you can wear Henleys from brands like Fresh Clean Threads with casual and semi-formal outfits, which is why it’s a men’s fashion favorite.

Wearing a Henley Shirt During Different Seasons

The way you wear a Henley is different depending on what season it is. And to make sure you style your Henley properly regardless of the season, here’s a quick guide to styling a Henley for different times of the year.


When summer comes around, you have the perfect opportunity to wear a Henley on its own. This is a great time to pull out a light-colored, short-sleeve Henley. You can wear the Henley tucked or untucked, depending on the event. On top of that, you can choose to wear it with shorts or your favorite pair of jeans.

Remember, summer is a warm season, and you will likely move around a lot when you go out. So, we recommend pairing your Henley with a nice pair of comfortable sneakers and sunglasses to really round out the look.


While there’s no rule against wearing light colors during autumn, earth-toned and subdued Henleys work best during this season. So, it might be time to shop for green, brown, and beige Henleys if you want to wear them during autumn. And while you can wear jeans with these colors, you can also step it up by putting on a pair of chinos.

If the temperatures start to drop, you can wear your Henley as a base layer. Then, you can put a jacket, jumper, or even a cardigan on top of the shirt. This creates a professional, classy, and timeless look that perfectly matches the season.

For this season, you can still wear sneakers with your Henley. But if you want to elevate your style, you can add some class by wearing it with a nice pair of boots!


You don’t have to put your Henleys in the back of your closet just because winter is coming around. This is one of the best times of the year to wear long-sleeve Henleys to maintain a casual look while still staying warm. 

Winter is the season of layers, and that remains true even if you wear a Henley. Just like in autumn, you can wear your Henley with a nice flannel and another jacket on top of it. But if you need to keep warmer, feel free to wear a jumper over the Henley before your jacket.

That said, when layering a Henley, it’s best to stick to a maximum of three layers. That way, you don’t end up looking too bulky.


For Spring, you can wear both bright and dark-colored Henleys. Since this season isn’t too cold or warm, you wear either short or long-sleeved options with a nice pair of jeans and chinos. You can even wear loafers with your outfit to add some more style to your wardrobe.

You may also like

Please help us continue to provide free, quality journalism by disabling your ad blocker on

Thank you for supporting our work.