How to Wear a Henley Shirt: Guys' Outfit Ideas

The base layer that's beyond basic

By Gabi Meyers | Last Updated: Oct 7 2019

If you know anything about team SG, it’s that we love us a man who knows how to wear a henley shirt (Taylor, specifically, loves this shirt style in a real and meaningful way).

And with good reason! The henley has all the ease of a tee with an added dose of maturity and style. 

Talk about a confidence booster!

Here at SG HQ, we’re all for a rakish polo or a well-loved t-shirt as much as the next all-female editorial team at an online menswear publication. But please don’t sleep on the henley. It might be time to add one (or, heck, ten) to your wardrobe.

Here’s what you’ll find in this henley shirt style guide…

  • what is a henley shirt?
  • what are the best kinds of henley shirts?
  • how to wear a henley in a light color
  • how to wear a henley in a darker color
  • our #SGapproved henley shopping picks

What is a henley shirt?

What sets apart a henley from a regular t-shirt or long-sleeve shirt are the buttons at the collar. In terminology of fashion-y people, these buttons “add visual interest” to an outfit.

A good henley shirt makes for a great base layer in cold weather, and it works just as well as a standalone top in warm weather.

What are the best henley shirts?

There’s a reason you so often see uber-famous celebrities photographed at the airport by the paparazzi in this wardrobe staple. They help make a guy look stylish without looking like he’s trying too hard. Because honestly, you aren’t!

Henley shirts can come in a variety of fabrics and textures from a waffle knit to a comfy-cozy slub jersey.

This season, henley shirts are getting even fancier with varieties in merino wool and even cashmere (check out our #SGapproved picks below for options at every price point).

The long-sleeve henley can take a casual outfit up a notch without sacrificing comfort. It just as easily makes a more formal look feel a bit more relaxed.

Below, how to wear a light-colored henley five ways:


How to wear a henley with a suit

Wear it well: Rework your office style for the weekend by swapping out your shirt and tie for a henley and scarf. It’s a fun and stylish way to switch things up with your most burly suit. Because the top buttons on a henley mirror those of your button up shirts, it makes a surprisingly elegant option to swap under your jacket.


How to wear a henley with chinos

SG Says: Channel a Hemsworth brother by layering your henley with a dressier vest.


How to wear a henley with jeans

SG Says: Layer the plaid shirt under the henley for a more casual take on the shirt and sweater combo.

Shop the best henleys in black


How to wear a henley with dress pants

SG Says: Mix your patterned trousers with a leather jacket for the perfect mix of gentlemen and bad boy.


How to wear a henley with joggers

SG Says: We love how the simple design of a henley feels just as at home on the set of Game of Thrones as it does on stage (or in the crowd) at an indie rock show. It’s why you can just as easily wear this shirt with a suit (as in Monday’s look) as you can for a day off. Cozy up for coffee in fleece-lined coat and sneaks and the obvious style-meets-comfort pant: joggers.

But that’s not all!

We wanted to give you twice the outfit inspiration, so we also put together five looks featuring a darker-colored (in this case, blue) henley.

When the weather’s not so cold, opt for a lightweight cotton style or something, like the Buck Mason style in the outfits below, with a linen blend, and you’ll be in business. We call it a “summer henley” even though it’s still long-sleeved.

How to wear a henley in a darker color five ways:


Wear a henley with dress pants and sneakers (yes, really!)

SG Says: Bring your warm weather henley to a casual office with trousers and a trendy jacket.

With vintage-looking sneakers, you’ll really be rocking an outfit with a capital “O” (as in “O-h-h-h boy do you look good!”)


SG Says: Let your henley mellow out bolder statement pieces, whether that’s a jacket, pants, or heck, both.


SG Says: Keep it cool and casual with cargo pants, trendy Veja sneakers, and a baseball cap for your next errand run.


SG Says: QQ: Can you wear a henley with shorts?


Layer a lightweight plaid shirt over your henley for the summer version of your favorite flannel.


SG Says: Wear a henley on your next date night with a clean pair of chukka boots, dark-rinse jeans, and your favorite lightweight jacket.

// Shop #SGapproved henleys //

Want more help selecting your perfect henley? The team at Style Girlfriend is ready to build your personalized shopping plan.