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How to Wear a Henley Shirt Like a Boss: Men’s Style Guide

You may take a look in your closet and assume that all shirts, regardless of color, material, and cost are exactly the same. But this simply isn’t true.

Men, in particular, have the uncanny ability to look good in almost everything they wear, as long as it is paired and accessorized with something smart. A simple henley shirt looks good with a pair of shorts, jogger pants, slacks, or jeans. The possibilities are endless.

Celebrities, in particular, have a thing with Henley shirts. Maybe it’s because guys who wear them always appear to have an elevated sense of style when being compared to your average Joe.

The shirt alone adds more to a guy’s sex appeal, and when you consider that the men making them popular are sex symbols like David Beckham, Channing Tatum, and Ryan Gosling, you know you can’t go wrong. If you are looking for a more formal, fashion-forward look, you can even pair it with a sleeved polo or blazer.

Reasons Why You Should Start Wearing Henley

Wearing Henley shirts bring out the natural good looks of every guy who wears them. Furthermore, they’re a fashion statement you can create, depending on how you choose to wear it and what you choose to pair it with.

If you do not have this shirt yet, get yourself one. If you already have one, do yourself a favor and get another one. Why do we recommend these so much? Below are the reasons why.

Henley shirts are perfect for travel

You can be yourself and showcase your fashionable, but casual side with Henley shirts. It is one hell of a comfortable outfit to wear when traveling.

They Show Off the Work You Put in at the Gym

As if this shirt wasn’t effective enough on its own, it also shows off all that hard work you’ve been putting in at the gym.

The shirt’s natural tendency to cling in all of the right places shows off the natural curves of the body without really exaggerating the muscles in an over the top way.

They go with your tucked preference

Some men like their shirt tucked while some men don’t. What makes Henley shirts so versatile to most men is the fact that they will look good in it whether they are tucked in, left out, or even half tucked.

They give you a more modern look

Henley shirts give a whole new meaning to the term matchy-matchy. The style of the shirt itself gives any man a more modernized look.

Henley Shirts Make Your Accessories Shine

Some Henley shirts have long sleeves that you can fold for a more stylish look. One good thing about this shirt is that folding its sleeves exposes your accessories, like watches, to add in more details to your overall style.

If you’re wearing a  Patek Philippe Platinum World Time or Vacheron Constantin Tour de I’lle, putting on a folded long-sleeved Henley shirt is the best way to highlight these accessories.

Henley is a Jacket’s Best Friend

When having a hard time choosing the best shirt to pair with your brand new jacket, just pull out a Henley shirt from your closet, put it on, and you’re all set.

Henley shirts are one shirt that will always look good when paired with just about any style of jacket.

What goes well with Henley shirts?

There are a lot of ways that you can get stylish with Henley shirts. You can mix it with any top or bottom. Whether you are looking for a formal or casual look, they work great either way.

There are men who would opt for the convenience because they look good in almost everything that you pair them with. Here are some proven great ways for you to look good in your Henley shirt.

Wearing Henley shirt with sa nice pair of Loafers

There are men that would opt for wearing Henley shirts with a matching pair of shoes. You may have a dark colored Henley shirt and have the same colored jeans for that single or two-toned outfit.

If you complete the look with a light or dark-colored pair of footwear that compliments the tone, you’re all set.

Cotton Cashmere Long-Sleeve Henley, $59.50

Wearing a Henley Shirt with Chinos

A nautical striped or just plain white Henley shirt paired with chinos is a more comfy, casual way of wearing the shirt. This get up is comfortable for men who have a lot of things to carry during their travel, and the shiny texture of your chinos is a good match to your striped-designed Henley shirt.

Pima-Modal Waffle-Knit Henley, $54.50

Wearing Henley Shirt with a Cardigan

This top works best with any kind of jacket, whether cotton or leather. When you are not comfortable wearing a coat and tie wardrobe for formal occasions, Henley shirts are the best alternative.

You may work or experiment on the color combination that will work best for your skin tone and body built, but you will surely find the right fit for this one.

Short-Sleeve Soft-Wash Henley, $34.50

Wearing Henley Shirt with Slacks

Whether formal or semi-formal, you can’t go wrong with Henley shirts. Nothing beats a guy who carries himself intelligently. You can accessorize your overlook by adding some stunning sunglasses and leather shoes.

This is one of the many good things about Henley shirts. You truly can wear them for any occasion.

Vintage Long-Sleeve Henley, $49.50

Wearing Henley Shirt with Jeans

Usually, men would opt to go for a t-shirt for their casual attire. However, with the arrival of several shirts designed for the same purpose, they began to have some variety to what they can wear. Having a Henley shirt for your top matched with a pair of denim pants, tattered or not, is definitely the perfect casual look. Some men would pair their jeans to a half-sleeved Henley shirt.

Henley shirts are a must-have for men. The stylish flexibility gives men various ways of wearing this top. They also give room for more room for them to experiment on what look will work best for them considering their body type and preference.

Get your own Henley shirt now! Who knows? This might be the start of you collecting varieties of this shirt.

Cotton Cashmere Long-Sleeve Henley, $59.50

What to Look for in your Henleys


Henleys are made out of cotton so you kinda don’t have so much choice but one thing you need to consider is the weight of the fabric. The lighter fabric weights should be worn in warmer climates like Summer and Spring. While thicker and heavy fabrics should be worn during cooler months like Autumn and Winter.You can get these in henleys in any versions you want. Lightweight summer weave where it feels like you’re just wearing your shirt to thicker ones that will keep you warm.


Like any other clothing, Henleys should have a perfect fit with your body and arms. You wouldn’t want it to be too loose since this will give you a sloppy look.  Henley’s shouldn’t have to be pinched for more than 2 inches on the side of the torso and not more than  1 inch around the bicep.

If you’re a slim guy you need to have the perfect fit especially if you opt to wear a long sleeve henley. If the fit is too loose on you it will make you look more slender and delicate that you really are and it’s a NO-NO!

Best Ways to Wear a Henley Shirt

Short sleeves henley and T-shirt are most likely similar so it means that they can be worn on their own or layered up with a jacket, a pair of jeans and sneakers.

Long sleeves are normally worn in cooler months and often layered with another piece of clothing like bomber jackets or hoodies. you can complete this look with jeans and sneakers.

How Many Buttons to Button on a Henley

So this question really comes down to the occasion and the environment.

But the standard rule is to button just the bottom button.

If you have a three-button henley, and you’re a bit conservative, then you can button the first 2 buttons.When wearing your henley, the goal should be to wear the shirt open and layered perfectly with another piece.
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