How to Style a Henley Shirt: Men’s Outfit Ideas

Henley Shirt

Last updated on November 28th, 2023 at 07:17 pm

A Henley shirt is a wardrobe basic in a t-shirt style with a buttoned-up round collar. It’s a versatile piece, providing a base layer for the winter months, and can be worn alone in the warmer seasons.

A Henley can come in different formats – a short sleeve Henley t-shirt or a longer-sleeved style for a more sophisticated touch to your basics. It has been loved by celebrities for years, and now it’s your turn to rock the look. Think of it as a modern take on the classic t-shirt, and you’ll soon be convinced!

Let us teach you a thing or two about Henley shirts!

What kinds of Henley shirts exist?

Henley shirts come in different lengths, sizes, colors and fabrics. To start off with, Henleys come in:

  • Lightweight fabrics – think lightweight t-shirt-like fabrics that may need to be layered in colder months.
  • Heavier fabrics – more suitable for fall and winter, and don’t necessarily need a lot of layering, apart from a jacket or coat.

Then, of course, they come in short or long sleeves. You may think of Daniel Craig in James Bond when you think of a longer-sleeved Henley t-shirt, while James Cordon is regularly seen in short-sleeved versions of the iconic shirt.

How can I wear a Henley shirt?


A Henley shirt can be worn alone with very little effort. A longer-sleeved style will look chic with a pair of jeans and sneakers. It’s a basic outfit but a classic. Choose whether you do up all the buttons or leave it open for a laid back vibe.

In the winter months, you can throw over your favorite jacket or coat for a timeless look. We can see a Henley shirt with a tailored coat for a sophisticated finish. Classic is the way to go!

READ ALSO: Jen Blanco: Instagram Star Age-Career-Boyfriend-Net worth

With a zip-up hoodie

Add a sportswear touch to your wardrobe by wearing your Henley t-shirt with your favorite zip-up hoodie. See it as making the most of your lockdown loungewear! No need to leave it for when you’re working from home, get out your best (and least tattered) hoodies!

Leave the zip undone a little to expose the striking Henley neckline. Then, throw on a pair of your favorite jeans and you’re good to go! This outfit will provide warmth without creating a bulky look.

Under a shirt

In the fall and winter time, we love to layer and make the most of all of our wardrobe essentials. You can also make use of your Henley shirt during this time, by rocking it under a shirt. A check print or floral print shirt will stand out, but by undoing the buttons of your shirt, you will still be able to show off your Henley shirt.

With dress pants

Mix up smart and casual by wearing your Henley shirt with a pair of dress pants. A simple check print pant can make your Henley appear even more sophisticated. To spice things up even more, we recommend throwing on a leather jacket for a rebellious attitude. Because though we love dressy outfits, you still need to be you!

With sportswear

There are sportswear-style Henley shirts that are ideal for workouts. As long as the fabric is lightweight and breathable, they can be teamed with your best sweatpants or gym shorts to create your go-to activewear outfit.

Don’t underestimate the power of a Henley shirt, it can elevate even the most casual of outfits in a flash. Now you’ve got the best tips and tricks out there, you can create some stylish outfits that will stand the test of time.

About The Author

Scroll to Top