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Does a Henley Shirt Go Well with a Jean Jacket?

Wearing a Henley shirt with a jean jacket is absolutely okay. It's actually a great combo and you can make many trendy looks with this pair. Check out how you can sport this style in various ways.

Man wearing a light denim jacket over a Henley shirt.

Can you wear a henley shirt with a jean jacket is a great question for men in particular, but also for women who want to update their unisex style. I say with certainty that you can wear a henley shirt with a jean jacket. Sure, the long sleeves are going to add bulk with a tighter jacket.

Therefore, you may want to size up the jean jacket. Fortunately, this does not hamper this look, since the denim is so stiff. However, that doesn’t mean your entire look has to be hard as nails. This is a great fashion choice for men and women, and it carries through the Seventies up to today with many trending looks.

Related: Do Henley Shirts Go with Dress Pants (Trousers)? | Is it Okay to Wear a Henley Shirt with Loafers? Dress Shoes? | Do Henley Shirts Go with Sneakers? If So, What Sneaker Colors? | Is it Okay to Wear a Henley Shirt with a Blazer?

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Get Hippie With It

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Here is one example of how anyone, male or female, can wear a henley and a jean jacket. Denim fashion is a hot trend for everyone, including those who are hippies in any sense of the word. Bell bottoms, am I right?

Add one to 100 soul patches and flower child pins to a jean jacket and you are as retro as they come.

Tossing a henley shirt under a vintage denim jacket, also called a trucker jacket, will easily transport your style back to the Swinging Seventies. Choose a henley that is made of patchwork or linen fabric and free of buttons for a more hippie-friendly style, such as this one sold on Amazon. Still called a henley shirt, this is a more hippie casual shirt that works great under a jean jacket as well.

Take Off the Sleeves and Go Longer

Man in a white henley shirt and baseball cap poses against the gray background.

The biggest issue with a henley and any jacket is the sleeves. Therefore, since the denim is going to keep you warm enough, take off the sleeves and work with a short-sleeved henley. If you do this, you are all set to be comfortable and stylish.

Unlike the more sophisticated cut of a blazer that does not go with a henley shirt, the denim jacket is far more relaxed.

According to Maxim, “Done the right way…[a henley shirt] can even be worn under everything from a denim jacket to a cotton blazer. Team yours with jeans and chukka boots, and you’ve got a look that’s ready for any and all things casual and cool.”

The use of a light-colored henley with a blue denim jacket and brown chukka boots with a pair of loose-fitting khakis that are in olive green is another great option here. Plus, thanks to the trio of buttons on the placard, a henley shirt can stand up on its own if you decide to chuck the denim jacket.

This makes the henley tee an excellent layering piece in fluctuating seasons and climates. For example, if you are traveling, the appearance of a short-sleeved henley tee and a denim jacket will hold up to the rigors of the road. You don’t have to worry about wrinkling the fabrics on either one and denim is tough enough to handle the wear and tear for cowboys, much fewer commuters.

In Neutral Tones of Blue and White

Man in a blue henley shirt and gray cap poses against a gray background.

One way to wear a henley shirt with a jean jacket is by layering it with coordinating colors. The jean jacket is most likely a blue tone, so go with a blue-hued henley or something in gray or white.

As referenced by Peter Manning NYC, an online apparel company for the not-so-tall guy in Manhattan’s Flatiron District, “If you wear [henley shirts] in relatively neutral colors like white, navy and grey, almost any color jacket will work on top.”

Here is the Peter Manning brand denim jacket with their line of henley shirts for men. They feature a denim jacket with a light blue henley shirt and cream chinos for a bright and refreshing look. This would be great in springtime when the winter coat goes into the back of the closet.

It’s as bright and cheerful as a Robin that has just hatched its first egg.

How Henley Shirts Work With Denim

Man wearing a white henley shirt and a jean jacket.

Overall, the choice of wearing a henley shirt that is made of waffle knit and a trio of buttons for the only adornment is easy.

Men and women, girls and boys, everyone wears henley shirts. It’s almost as popular as the tee-shirt in terms of appearance and accessibility in stores. Therefore, finding a henley shirt is easy. So is finding a denim jacket.

Jean jackets have been one of the most popular pieces of clothing to ever come out of the US. The jean jacket is an American-style staple as noted by Levi Strauss and Co. and one that rockers, rappers, cowboys, and financial workers on Wall Street all wear. Working and playing, styling and profiling, the denim jacket have its roots in Americana.

Therefore, to pair an easy-to-wear henley shirt, which has an iconic baseball player-style with its button placard and two-toned sleeve-to-body option, with a blue jean jacket is easier than saying it. The henley was designed in Britain during the Industrial Revolution as a uniform for rowers in the 1880s. But it was not until the 1990s that the henley shirt became a cool and hip addition to urban closets.

Both of these clothing items are workhorses and they scream blue-collar, quite literally in the case of the denim jacket. Wearing these together makes sense in a subliminally historical way. You would not, for example, wear a henley shirt under a doctor’s white coat. That would be atrocious.

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