How To Wear a Henley Shirt (5 Outfit Ideas)

One of the most versatile pieces in our collection is our Henley Shirt. It's a wonderful warm base layer in the winter months and perfect as a standalone shirt when spring hits.

The Henley has long been the MVP of celebrities and the stylists who dress them. The shirt has its roots with the Henley Regatta, a premiere rowing competition where the oarsmen utilized the extra ventilation offered by the ability to open the collar.

Henleys are the unstoppable workhorse of shirts. And we don't just say that because of their old-school vibe, but because they can be worn in a ton of different ways, with a ton of different stuff, and give you the added benefit of instant appeal.

-GQ magazine

The buttons beneath the collar elevate the Henley beyond a standard t-shirt and provide an extra dose of visual interest in your outfit. As with any great style boost, wearing a Henley doesn't look like you're trying too hard, and anyone can pull it off.

Here are a few of our favorite ways to wear a long sleeve Henley:

#1: Just the Henley

Why complicate things? Henleys look great on their own with a pair of casual pants (like jeans, chinos or cords).

White Henley shirt with jeans

Even a basic outfit is boosted with a Henley shirt. It's just one notch up from a t-shirt in terms of uniqueness.

Whether you choose to button all three buttons or none at all is a matter of personal preference.

Another advantage with the Henley is that it provides a substantial layer of warmth without adding bulk, ideal for underneath a thick winter coat.

#2: With a Hoodie

If you need to add a bit more warmth to a casual outfit, just throw on a simple cotton hoodie.

Henley under hoodie

This produces less bulk and insulation than an actual jacket, but it's still a comfy, laid back look that any guy can pull off.

Casual henley outfit

A grey or navy blue hoodie will work with pretty much any Henley shirt you'd like to wear.

#3: Underneath a Jacket

Of course, you can wear almost any type of outerwear over a Henley. Rugged pieces like leather jackets and field jackets work especially well.

Henley shirt with field jacket

We really love this look in fall and winter, as transition weather calls for a shirt like a Henley. The beauty is its simplicity.

Grey Henley with olive field jacket

If you wear Henleys in relatively neutral colors like white, navy and grey, almost any color jacket will work on top.

#4: Under a Button Up Shirt

We are proponents of taming patterns with solids. Here the Henley is a solid choice to layer underneath our plaid Flannel Work Shirt.

Henley under flannel shirt

Notice how the three buttons at the top add a small detail to help elevate the outfit. As always, shoe choice is key, and these boots in a lighter shade of brown pair well with the other more muted colors, like medium wash blue jeans.

Mixing contrasting fabrics can have the same nice effect as contrasting colors. Here the textural differences of our Flannel Work Shirt over the slub cotton Henley does much of the work in providing some visual interest, even with basic solid colors throughout the outfit.

#5: Layered Up

The Henley works really well as a warm base layer with multiple heavier layers on top. For example, when it's too cold for just a field jacket, throw on a lightweight quilted vest for extra warmth and style points.

Layered casual fall outfit

You could swap the field jacket for leather, or the vest for a comfy flannel work shirt. Either way, there's something magical about wearing three layers (shirt > middle > outerwear).

Two is okay, and four can be too busy. But three? It's just perfect. And the Henley is an excellent base layer upon which to build a great casual outfit.

How do you wear your Henley shirts?

We hope these Henley shirt outfit ideas give you some inspiration. If you don't have a Henley in your wardrobe, we highly recommend getting your hands on one (or three).