How To Wear a Henley Shirt for Men After 40

How To Wear a Henley Shirt for Men After 40

Henley shirts are men's shirts popular in the 19th century and are still worn by men in the 21st century. Today, it is most commonly associated with a college sport called "The Game." You named the shirts after a British naval officer who died while serving on HMS Rattlesnake in 1799. The name "Henley" comes from the ship's captain, John Henley.  A henley is a collarless shirt with two or more buttons. It can be short-sleeve or long-sleeve and is typically made from cotton. Henley shirts are buttoned-down, usually featuring two or three buttons on the front of the shirt and a plain collar. They are generally worn tucked into pants or a jacket.


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


A henley shirt and dark brown chinos are the kind of a winning off-duty ensemble that you so desperately need when you have zero time to plan an ensemble. Black and white checked canvas slip-on sneakers are a stylish addition to your look. Those of you wondering how to stay stylish after 40, you have your answer.


A henley shirt goes well with black jeans. Add tobacco canvas low-top sneakers to the mix, and the mix is a big boost for those who have doubts about wearing casual as a grown-up gentleman.


This off-duty pairing of a henley shirt and navy shorts is a lifesaver when you need to look chic but don't have much time to put together an outfit. A nice pair of black leather oxfords is the easiest way to bring a touch of sophistication to your look. When it comes to style skills for mature men, this combination is ideal.


What you're looking at now is undeniable proof that a loose Henley shirt and navy shorts look great together. Don't know how to wrap it up? Add a pair of navy and white canvas high-top sneakers to the look for a more laid-back effect. Wondering how to master casual style in your 40s? This set is a practical illustration.


A long-sleeve Henley shirt paired with charcoal shorts is the perfect outfit for the casual man. Complete the look with a pair of dark brown suede desert boots to elevate the style factor of your outfit effortlessly. Overall, this is the perfect showcase for effortless style for men over 40.



The charm of the henley is far beyond people's imagination. Buttons add dimension and visual interest, and are a staple in every man's wardrobe. A henley can be dressed up with a blazer or suit, or casual with a denim jacket or flannel. The variety of colors available for flannel also makes it a great piece to wear on its own. The beauty of the henley is that it can be worn every season. Because there is so much variety of style, you can find the perfect henley for any weather. Pay close attention to the fabric weight when shopping for your henley. Opt for lightweight henleys in the summer and heavy-weight in the winter.

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