Wearing and Choosing Henley Shirts

By Jack Prenter / February 1, 2018
Henley shirts feature image

When it comes to men’s style it’s often best to create your wardrobe out of a few specific basics that you can build around. For example; pieces like dark wash jeans, polos, henley shirts and white dress shirts are incredibly versatile and therefore worth investing in.

By investing in both the quality and quantity of these types of items you can significantly improve your own wardrobe. After all, the vast majority of the time you will be wearing pieces like this and so not only does it make dressing easy, it also ensures that you look fantastic at all times.

What is the Henley Shirt?

The henley shirt is an essential in every mans wardrobe. This type of shirt is incredibly similar to a t-shirt, only with a placket beneath the rounded neckline, which has between two and five buttons. In many ways it closely resembles a polo shirt without a collar.

However, the material is often the same as a t-shirt but the neckline is usually thicker and more defined that you would find on most t-shirts. This piece is so named because of the uniform which English rowers would wear in the Henley Royal Regatta, a famous rowing event in the UK.

Many fashion experts give credit to Ralph Lauren for popularizing them in contemporary culture and for this reason the company is still a good source for them.

How to Wear a Henley Shirt

Knowing how to wear a piece of clothing is half of the battle. It's impossible to just buy one item if you're not sure how you're going to match it. Instead, it's wiser to either have a pair of pants in mind to go with it, or to buy them alongside the shirt.

As mentioned previously, henley shirts can reasonably be treated as smart t-shirt or a polo shirt. This means that you can wear them with jeans, khakis, chinos and even shorts. They are utilitarian and can easily be dressed either up or down, making them a great investment for the stylish man.

Presuming you choose a standard color you should get plenty of versatility out of it. The following two outfits are slight variations on the same idea, one that most men can wear week after week, a shirt combined with jeans.

What's really fantastic about these two outfits is that they could be worn with a range of footwear including brown dress shoes, Chelsea boots, sneakers, running trainers, chukka boots, suede shoes and even loafers.

This versatility is what we think you'll love about a henley.

Gray shirt with light blue jeans that are faded

In the above outfit the model is wearing a light gray henley made out of a relatively thick cotton and spandex blend. This blend is what gives the shirt a tailored and fitted looking, stretching slightly to your body shape and giving you a wonderful look.

Although 100% cotton can be softer, adding a little spandex can help the clothing to fit better. The color is also wonderful, a neutral option that can be worn with any color denim. For most guys a gray color like this is a worthy investment because it can be worn with a greater number of outfits.

The jeans he is wearing are a light blue wash that have been faded slightly across the thigh to give it the streaky look. This style of denim is also incredibly versatile and while it is rather casual it could be dressed up with leather loafers or smart suede shoes.

This particular outfit would be great for casual events like going out to a bar or perhaps even on a date. The henley gives you plenty of options and as you can see this model has opted to leave the top button open. For most guys leaving one or two buttons open is best, any more or less and it can look peculiar.

Green shirt with a dark wash jean

The second outfit is similar but slightly different, not only is the model wearing a green shirt, he's also opted for a dark wash pair of jeans. This look is arguably much smarter, more professional and could be worn to the office and even to events.

Undoubtably the henley shirt isn't a dressy option, it's definitively casual, but the pants and shoes that you wear with it will define whether it's extremely relaxed or more smart.

We could see this outfit being worn with a brown leather brogue or oxford shoe, with a dark overcoat and watch. Another alternative would be a black leather jacket and suede shoes, combining for a fantastic outfit for evening events that don't require a button-up shirt.​​​​

How Should it Fit Your Body?

As with both a t-shirt and a polo, your henley should be slim throughout. In reality this means that you should feel a ‘hug’ from the fabric across your shoulders and even a little in the chest and back. Clearly, it shouldn’t be uncomfortable or skin-tight, instead, search for a slim but comfortable fit.

A good indicator of this is the seam of the sleeve and the body of the shirt, this seam should sit right at the point of your shoulder where it angles from horizontal to vertical. If the seam is closer to your neck then you need to go a size up, if the seam is beyond this point you should go a size down and see how that fits.

Similarly with the length and the body of the fabric you should pick a reputable brand that makes high quality clothing because this is generally going to give you the best fit. Cheaper brands tend to make baggier and shorter tops whereas higher quality brands create a tailored, slim and long fit that is ideal.

Choosing a Fabric

The vast majority of the options that you will find are 100% cotton, but that doesn’t mean that all products are made alike. In fact, the quality and quantity of cotton used can have a considerable impact on both the feel and the look.

Again, investing in a more expensive piece will generally give you a superior feel and look. But the main choice that you must make is in the thickness of the fabric itself. Do you want it to be thick or thin?

Thick gray cotton shirt with a white stripe and white buttons

Made out of a thick cotton and polyester blend, this shirt would be ideal for slightly colder climates. Unlike most shirts this has a defined white embellishment along the inside of the placket. 

If you are living in a warmer climate like California or Asia you might prefer a thinner material that uses less cotton. Whereas if you are based out of Toronto or Sweden you could opt for a heavier cotton blend that has the feel of a light sweatshirt.

Both of these options are available and you can easily tell by looking at the garments online and by reading the descriptions of the products which generally will give you information about the thickness.

Long or Short Sleeved?

Most fashion houses offer this style of shirt in both long and short sleeved versions, but which should you choose? In our opinion, the long sleeved version is far superior. The main problem with the short sleeved is that is lacks ‘balance’ across the body.

The reason for this is the open collar and buttons which attract your attention. We tend to associated buttoned shirts with long sleeves and for this reason they can look top-heavy and obscure. Instead, the long sleeves help to balance the buttons out and give a more elegant silhouette.

For this reason, most men will look much better in long sleeves, particularly if you are holding extra weight. Rolled sleeves look great and choosing a long sleeve gives you this option.

It’s fair to say that short sleeves are more casual and therefore the primary reason for choosing them would be to wear with an incredibly casual outfit like shorts and boat shoes. However, for wearing with smart jeans a longer sleeve is more desirable for most men. But at the end of the day, you should pick whichever you like the most.

Different Colors

When it comes to color you have a huge selection. This style of top can be found in almost any color, including obscure shades that you might never have thought of. However, that certainly doesn’t mean that you should choose them.

In fact, the vast majority of men suit only a few colors and sticking to these ensures that not only will you look good, but they will also match most of your other pieces of clothing. Making sure that new pieces of apparel match your existing wardrobe is vital because if it doesn’t it’s unlikely that you will wear it regularly.

Therefore, sticking with solid colors like navy, gray, black, white and green. Within those colors you can explore a variety of shades and material patterns so that in reality your choice is much more varied than you might assume.

The color that you pick should depend on your skin color and the other clothes that you wear most frequently. Men with lighter skin often look best in grays, navy and greens, those with olive skin suit light neutrals like light blue and gray, as well as purples, men with dark skin can wear nearly every color but look particularly great in bold and deep shades.

But while the tone of your skin is important, so are the clothes that you plan to wear with it. If the rest of your wardrobe is filled with navy or black, it might be best to choose another color that can complement that. Similarly, if your favorite jeans are a light blue you probably don’t want a light blue henley to go with it, instead, a darker gray, black or beige could look fantastic.

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