How to Wear a Henley

How to Wear a Henley

You can dress up or down the versatile and stylish henley shirt.

But how do you wear a henley? Henleys are considered casual, they typically pair well with jeans or chinos. Often, you can leave the top few buttons undone to create a relaxed and effortless look. 

In this blog post, I'll go into more detail on outfit ideas for Henleys. I'll also cover whether you should wear anything under them.

What Is a Henley Shirt?

A Henley shirt is a type of button-down shirt named after the English town of Henley-on-Thames. It typically has long sleeves and a collar, but the distinguishing feature of a Henley shirt is that it does not have a traditional placket.

Looking for a henley that fits perfectly to your body? Check out our collection of fitted henleys right here.

Instead, the shirt has a slit at the neckline that is usually fastened with one or two buttons. This design gives the shirt a more casual look, making it ideal for weekend wear or layering under a jumper or jacket.

Henley shirts are available in various colours and warm fabrics, from lightweight cotton to wool and flannel. They can also be found in solids/patterns, and can be tucked in or out making them versatile enough to suit any style.

So whether you're looking for a casual alternative to a button-down shirt or want to add something new to your wardrobe, a Henley shirt is a great option.

wearing a white henley by tapered menswear

White Tapered Fit Henley

Do You Wear Anything Under a Henley?

There's something about a henley that oozes everyday cool.

Whether you're wearing it on its own with denim or layer it under a jacket, it always looks effortlessly put together. But the big question is, do you wear anything under a henley?

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Mostly, it seems like guys are divided on this one. Some say that a henley is a best-worn solo, while others prefer to layer it over a tee or under a button-down shirt.

How to Layer a Henley

Even a few guys out there like to rock a tank top underneath their henleys. Ultimately, it comes down to personal preference. If you're comfortable going sans shirt, then go for it. But if you feel more comfortable with an extra layer, there's nothing wrong with that.

No matter how you wear it, ensure your henley fits well and looks good on you. After all, that's what really matters.

White Tapered fit henley. A henley that is fitted for a v taper physique

White Tapered Fit Henley

Are Henley Shirts Attractive?

Henley shirts are a type of shirt that has a button placket that extends partway down the chest.

Henleys are usually made of knit fabrics such as cotton or wool and can be worn as casual and dressy shirts.

While their popularity has waxed and waned over the years, they have experienced a resurgence in recent years thanks to their versatile style.

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Many men find Henleys attractive because they are comfortable and easy to wear. They can be dressed with trousers and a blazer for a more polished look or worn with jeans for a more casual vibe.

In addition, Henleys often have a relaxed fit that is flattering on many different body types. A Henley is an excellent option if you're looking for a shirt to wear on a date or just something to throw on for weekend errands.


model wearing a white slim fit henley, holding a bag with chinos by tapered menswear
White Tapered Fit Henley


Whether or not a henley shirt is attractive comes down to personal preference. Some people find them very attractive, while others prefer collared shirts.

So if you're unsure whether or not henleys are for you, why not give one a try and see how you feel? You might be surprised!

Are Henleys Still in Style?

Henleys are still in style. They've been enjoying something of a style renaissance in recent years. Thanks to their casual yet stylish look, henleys can be worn in various situations, from the office to the weekend.

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When to Wear Henley Shirts

Henleys pair well with denim and khakis, making them highly versatile. Finally, a henley is a great option if you're looking for a shirt that will never go out of style.

It's the perfect blend of casual and dressy and can be dressed up or down depending on the occasion.

Whether you're looking for a new work shirt or just something to wear on the weekends, a henley is a great choice. So go ahead and add one (or two) to your wardrobe - you won't regret it!

Wear a Henley shirt when you want a comfortable, stylish option that works well in casual settings, transitional weather, and for layering. Dress it up or down to fit the occasion.


model wearing a white slim fit henley by tapered menswear

White Tapered Fit Henley 

Is a Henley Smart Casual?

A Henley is a shirt that was initially designed to be worn as an undergarment. It has a button placket that extends down from the collar and usually has long sleeves.

A henley is generally made from either cotton or wool, and it comes in a variety of colours. In addition, you can find henleys with different neckline styles, such as a V-neck or a round neck.

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The term "smart casual" is difficult to define because it means different things to different people. For some, a smart casual dress code means no jeans or trainers, while others suggest looking neat and put-together.

For example, a henley can be considered smart casual attire. It is versatile and can be dressed up or down depending on the occasion.

If you wear a henley to work, pair it with dress trousers and shoes. You can wear a henley with jeans and loafers for a more casual look. Whether you dress it up or down, a henley is an excellent choice for smart casual attire.


model wearing a white slim fit henley with chinos by tapered menswear
White Tapered Fit Henley


Are Henleys Formal?

Henleys are a bit of a style chameleon; they can be dressed up or down, depending on the occasion. So, are henleys formal? It depends.

If you opt for a standard white henley, it will lean more casual.

But if you choose a henley with more unique details, like an intricate stitch pattern or buttons made from mother-of-pearl, it can work in a more formal setting. Of course, fabric choice also plays a role.

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A henley made from linen will have a more relaxed feel, while one crafted from wool will look slightly sharper.

How to Wear a Henley T-Shirt

Ultimately, it's all about considering the individual elements of your henley and how they come together to create an overall look. With that in mind, you should have no problem nailing the perfect vibe for any occasion.

As you can see, there's no wrong way to wear a henley shirt! Whether you dress yours up or down, layer it or wear it on its own, there are endless possibilities when styling this versatile piece. So go out and experiment with different looks until you find the one that's perfect for you!

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The World’s First V-Taper Cut T-Shirt

Fully fitted in chest and shoulders whilst tapering sharply down, giving a tailored look. No more bagginess in the waist.


navy tapered fit t-shirts showing a tailored look and feel


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Moulds to your arm and cut to the optimal length to emphasise the bicep peak.


navy tapered fit t-shirt closely fitted in the biceps


Stretch Cotton

Super soft, breathable and allows complete freedom of movement.