When men start paying closer attention to how they dress, one of the first things they do is tuck in their shirts. Tucking in a shirt is great for shaping your body and keeping a clean look with any outfit.

But one debate resonating in the world of men’s fashion is whether or not you should tuck in a Henley.

Henley’s are versatile shirts that you can easily dress up or down. These are great picks for casual, business casual, and smart casual outfits. But are you supposed to tuck in a Henley?

We’re answering that very question in that article while also giving out a few tips on how you can style a Henley and instantly elevate your fashion game.

Read on to learn more.

What Is a Henley?

Henley’s are collarless pullover shirts. They typically have a round neckline and a vertical opening with buttons. Despite not having a collar, these shirts are not as casual as regular t-shirts and can easily be worn with many outfits.

There are two types of Henley’s: short and long-sleeved options. You can wear either Henley with casual, smart casual, or business casual outfits, which is why they are a men’s fashion staple.

Ideally, a Henley should be well-fitting and highlight your body. Henley’s design is excellent at highlighting a person’s neck and focusing on their upper body, as you can see here: https://freshcleantees.com/collections/short-sleeve-henleys

However, they may not be the best option for larger and heavier men because they can accentuate a large neck and round features.

Should You Tuck In a Henley?

Whether or not you should tuck in your shirt is usually dictated by its length. And because Henley’s have a flat hem, they are best worn untucked. So, when buying a Henley, pay attention to the length and ensure that it ends at about the midway point of your fly, which is a good rule of thumb to follow.

If you feel like you should tuck in your Henley, that’s a sign that the shirt is too long for you. That said, many men are starting to tuck in their Henley’s to further accentuate their bodies, and it can make for a cool look.

While the general rule is that Henley’s should be untucked, don’t be afraid to experiment with your fashion. And if you feel like the Henley looks good when untucked, don’t be afraid to wear it that way!

Different Ways to Style a Henley

Here are some ways to wear a Henley and take your fashion to the next level.

As a Standalone Shirt

Henley’s are simple but very stylish shirts. So, you can pair it with a pair of jeans and get a stylish and simple look. Henley’s pair great with dark blue jeans or joggers for a casual, everyday look.

Under a Flannel

You can wear your Henley under a flannel if you want a cozier feel and a more rugged look. When you wear flannel on top of a Henley, you create a very casual layered look that’s perfect for when temperatures start to drop.

With a Suit

It might not be an obvious pairing for a suit, but Henley’s works great when you want to dress down your suit and still look very stylish. This is classier than wearing a suit with a t-shirt but not as formal as a dress shirt.


The general rule with Henley’s is that you shouldn’t tuck them in. So, for casual looks, it’s best to keep the Henley untucked. However, there are times when a tucked-in Henley can look good, especially when the fit is right!