Tips for Dressing Up a Henley Shirt

We have all seen a henley shirt, even if we don’t know the proper name of it. But even if you’re not aware of the name, a henley can be a very important part of your wardrobe, especially in parts of the world that get a bit chilly during the fall, winter, and spring.

What Is a Henley Shirt?

A Henley shirt is a type of casual, collarless shirt that features a partial button-down placket at the neckline. It is typically characterized by its round neckline with a placket that extends a few inches down the chest, and it is often fastened with two to five buttons. Henley shirts can be short-sleeved or long-sleeved and are typically made from lightweight materials such as cotton, which makes them very comfortable and perfect for casual wear. They are known for their versatility and are often chosen for their comfort and relaxed, yet slightly more stylish look compared to a basic T-shirt.

Dressing up a henley shirt is a great way to achieve a smart-casual or even a semi-formal look. But if you are wanting to “dress up” your henley and make it appropriate for a bit more formal wear, you have to know what choices to make.

How To Dress Up Your Henley Shirt

Henley shirts are commonly available in a variety of colors and fabrics and are popular choices for a wide range of casual activities, including lounging, going out with friends, or even as part of a semi-casual outfit when paired with jeans or chinos.

If you are looking to include your henley in an outfit that is perhaps more formal or appropriate for business, you can absolutely do that. It just takes some forethought and planning.

Choose a Quality Henley

Before you can do anything else, you need to start with a well-fitting, high-quality henley shirt. Opt for neutral colors like white, gray, or black for a versatile look, or choose a more muted tone like navy or olive for a slightly dressier vibe. And you can never go wrong with a stretch jersey henley, which will be comfortable, look classy, and remain breathable.

Pair with Dress Pants

Dress up your henley by wearing it with a pair of well-fitted dress pants. Dark-colored trousers like charcoal or navy work well for a sophisticated look. Choose flat-front pants for a cleaner appearance. It is very important that your henley fits really well if you are going this route, as an oversized henley doesn’t look appealing with dress pants.

Tuck It In

To elevate your henley shirt, tuck it into your dress pants. This small change will instantly make your outfit look much more polished and presentable. You can always use a leather belt to keep it in place, which will also add a touch of class.

Add a Blazer or Sport Coat

Another way to dress up your henley is to layer a blazer or sport coat over your tucked-in henley, giving you a smart or business-casual appearance. A navy blazer is a classic choice, but you can also experiment with different colors and textures.

Choose Dress Shoes

Complete your dressed-up henley look with a pair of polished, presentable dress shoes. Oxfords or derby shoes are always excellent choices, but you will want to make your choice based on how good they look and the color they come in. Also, make sure they match your belt for a totally cohesive look.

Maintain Grooming

A dressed-up outfit is complete when you pay attention to grooming. Make sure you're clean-shaven or have a well-groomed beard, and your hair is neatly styled.

Confidence is Key

You have to believe in yourself, always. The key to dressing up any outfit is to wear it with confidence. How you carry yourself can make a huge difference in how others perceive your style.

Experiment with Fabrics

Consider different fabric choices. A henley made from a high-quality material like merino wool or a silk-blend can give your outfit a more luxurious feel. 

Occasion Matters

You should also always keep in mind the occasion that you’re dressing up your henley for. While a henley can be dressed up for a semi-formal event, it may not be appropriate for very formal occasions. There may be a time when you have to make a different choice, and that is totally okay.

Layer Thoughtfully

Layering can add depth and style to your henley outfit. Try adding a light sweater over your henley and underneath a blazer for added texture and warmth. 


Always remember that dressing up your henley shirt is all about balancing your comfort as well as your style. By following the steps we have laid out for you, you will be able to achieve a polished and sophisticated look while still feeling comfortable in your clothin