7 rolled up men's henleys from various brands.

What a Henley Can Do For You

Henley shirts are a longtime favorite for guys for two simple reasons: they’re comfortable and they look good. That’s like a meal that tastes good and there’s a lot of it, a winning combo.

Luckily, you can do a henley for every season and with a wide range of outfits. Whether you’re looking for a guide to wearing henleys or you’re just wondering what the heck a henley even is, we’re here to help.

What’s a henley?

A henley distinctly has 2-5 buttons on the upper chest like a polo but without the collar. They come in both lightweight and thick fabrics and both short-sleeve and long-sleeve. The name originated from the English town of Henley-on-Thames where rowers used a similar-looking uniform.

Why are they so popular?

Henleys are extremely flexible. The short-sleeved, thinner fabric variations (with its distinct button arrangement) are basically t-shirts taken up a few notches on the cool scale.

Long-sleeve henleys on the other hand, layer well with sport coats and other light jackets. If the weather’s nice, you can also rock the long-sleeve henley on its own with the sleeves rolled up.

Oh, and did we mention they usually come in comfy cotton (or cotton blend) and in an array of colors?


Since the henley is super simple (basically just a t-shirt with some buttons), it’s going to be pretty noticeable if the fit is off. So, make sure you aren’t swimming in it, nor is it making you look shrink-wrapped. This gets even trickier for guys on the ends of the spectrum where there’s a greater risk of an ill-fitting shirt accentuating your less-than-flattering qualities.


This one’s much easier. You don’t need to be a fashion genius to pair lighter materials with warm seasons and thicker with the cold. Most people probably associate the henley with the thicker thermal materials the shirt is associated with, but lighter ones are readily available if you’re looking to rock it year-round.


This is the henley’s wheelhouse. This style looks rugged, masculine and just plain awesome layered under a jacket. So, do it. The button placket also makes for a nice detail in the outfit.