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How To Style and Accessorize a Henley Shirt?

October 04, 2022 by Jeremy Lindy

If you don't have a Henley t-shirt, it's time to get one or the fall! It's perfect as a canvas for layering and looks stylish on its own too.

A Henley is a collarless tee with a button placket down the collarbone. The unusual neckline was initially created to provide comfort and ventilation for athletes. And while sports fashion has moved forward, the collar remains a fantastic design element. 

The t-shirt helps you stand out from the crowd and flatters the body, but if you're not sure how to wear it, worry not because we've got your back.

The best choices for the Henley

The Henley shirt can be long- or short-sleeved, and it's up to you to choose your preference. The key to looking good is the right fit and high quality. Fresh Clean Tees has some great Henleys in a variety of colors and fantastic fits, so make sure to check them out here freshcleantees.com/collections/short-sleeve-henleys.

Pair it with a laid-back jacket

With the cooler fall weather, there's no better way to wear your Henley than under a laid-back jacket. That can be anything from utility to denim to puffer to leather jackets. Henley tees are more casual, so they'll work perfectly with any of those garments.

If you're into versatility (like we are!), we recommend stocking up on a few neutral-colored t-shirts so that they work with any jacket color or pattern. 

These are some of the best men's jackets to go with a Henley:

  • Utility

  • Denim

  • Leather

  • Puffer

  • Parka

  • Bomber

  • Suede 

Under a hoodie 

Another casual way to wear your Henley is under a zip-up hoodie. Hoodie adds extra warmth and is comfortable and laid back.

We love this look for running errands or grabbing weekend lunch at your favorite spot. Choose classic colors such as navy, olive, or maroon and pair them with simple gray, black, or white Henley, but feel free to experiment with something less common, like e.g., purple or mustard yellow.

We recommend opting for a tailored hoodie instead of an oversized one.

With a casual button-down shirt

A few looks are as classic as a Henley under a button-down flannel shirt. 

The look is casual yet sexy and stylish (hot lumberjack, anyone?) and will work for anything from meeting your pals at the pub to going on a weekend hiking adventure. 

Here are some of the best flannel shirt colors to go with a Henley:

  • Plain 

  • Checkered

  • Red 

  • Blue 

  • Black 

  • Green 

  • Brown

Bottoms

Now that we've settled on the best tops to wear with a Henley tee let's move to the bottoms. 

Jeans 

Jeans are a classic and will look great paired with any of the tops mentioned above. 

Whether you style them with a jacket, hoodie, or flannel shirt, you will have the perfect outfit for any casual outfit.

The following types of jeans are the most suitable for the Henley:

  • Straight leg

  • Slim straight

  • Relaxed slim

  • Wide leg

Chinos

Chinos are the perfect alternative to jeans when you want to look a little more put together.

Go for slim fit or stretch fit, as they're the most flattering and, psst, make you look a little taller!

We recommend the following color options for maximum versatility:

  • Navy 

  • Beige 

  • Khaki

  • Grey 

  • Black

Cargo pants

Cargo pants are back, and we love them in combination with a Henley. Opt for classic khaki or grey pants and wear them either with plain long-sleeved Henley or layer with a flannel shirt or a classic blue denim jacket

Accessories

One of the cool things about Henley tees is that they're effortless to accessorize. And no, you don't have to go full Johny Depp to have an effect! 

Your favorite watch will look great with a short-sleeved Henley or sleeves rolled up, along with leather or metal bracelets. 

And as the neckline exposes a little bit of your chest, it's perfect for minimalistic necklaces or pendants. 

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