How Tight Should a Henley Fit?

Learn how to style one of the most versatile pieces out there.

RAG & BONE Orange Waffle Devon Henley, Courtesy of SSENSE

Trends come and go, but Henleys are forever. This style staple is about to revolutionize your wardrobe, and for all the right reasons. Bored of the same old t-shirts? Well, you’ll definitely want a Henley!


See it is a suave, older brother of the t-shirt. It ticks so many boxes – it can work for smart casual looks, and even on lazy Sundays. The Henley is one of the most versatile pieces a man could ever own, so it’s well worth investing in a few!

The history behind the Henley

The Henley hasn’t always been a sign of impeccable style. Back in the 1800s, it was actually an undergarment, before shortly being chosen as part of rowers’ outfits in the UK. The cotton fabric made it perfect for cooling down rowers after breaking out a sweat in their races. The tradition was that the losing team had to give their Henleys to the winners!

How did it become a style staple? Ralph Lauren saw a vintage Henley and made it his own in the 1970s. He added his iconic Ralph Lauren logo to his pieces and made the Henley a thing. It was hugely successful and today, many brands sell Henleys as part of their collections.

Why wear a Henley?

As we mentioned earlier, the Henley is a versatile piece of clothing. It can work in the summer and winter times, just styled up differently! Plus, there are short sleeve and long sleeve Henley shirts for men.

Much like the t-shirt or the polo shirt, it is a fundamental part of a man’s wardrobe. Whether it’s for work or a date night, the Henley will never let you down!

RAG & BONE Gray Cotton Henley, Courtesy of SSENSE

How to style a Henley

A Henley works every time! Don’t know how to style it? Let us give you a few ideas:

With some flannel

Come fall and winter, you can never go wrong with some flannel. Our advice? Wear your flannel shirt open with your Henley underneath for a cool yet warm look. This will allow you to layer up without looking bulky.

Under a chic shirt

Shirts are so polished, and are perfect for looking sharp! However, in the winter time, you need an extra layer for them to work. The Henley is a more sophisticated take on the t-shirt, and will look even more so under a shirt.

Under another button-up

Go for heritage vibes by wearing your Henley unbuttoned with a button-up fleece over the top. This has all the countryside feels we love! Team them with your favorite pair of jeans, and this look is perfect for family walks on Sundays.

Smart casual with chinos

Nailing smart casual is an art. Be a master in it by combining your Henley with a pair of neutral-toned chinos (we’re thinking khaki or beige) and switch things up with a pair of white sneakers.

How should the Henley fit?

Getting the right fit will allow you to create a sophisticated look, even when it’s casual. When everything fits just right, you look your best. You’ll want to make sure, no matter what you’re wearing, that it flatters your frame, and the Henley is no different.

Like a good t-shirt, the Henley shouldn’t be too big or too small. Either you’ll look like you’re in denial and still wearing clothes from your teenage years, or the Henley will drown you. To get the perfect look, the Henley needs to fit in all the right places.

Shoulder seam

Like with t-shirts, the shoulder seam has to be just above the shoulder. The sleeves should be lightly loose to allow free movement. If they are too tight, you’ll just feel comfortable, and trust us – it will show!


To perfect your looks, you need to ensure that your Henley fits right around the chest. Anything too tight will look pretentious, while something too large in the chest will give you 90s’ Eminem vibes. If they fit right around the chest, you’ll look super muscular and fit.


The Henley should be a straight fit, and therefore have a little room around the torso. If your Henley is too close for comfort, then it’s not the right fit. It’s all about finding that balance.

Arms and sleeves

Like the shoulders, the sleeves need to fall well. They should be a little loose and allow you to move however you want. The sleeves should lightly hug your arms, but shouldn’t be tight or stuffy. You also need to ensure there’s no access fabric, or it’ll unbalance your body.

Now we’ve revealed the secrets to nailing the Henley, it’s your turn to create some epic looks with this wardrobe classic. Get a Henley that is in high quality fabric that will stand the test of time – that way you’ll treasure it for years!

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Jing Boran

Jing Boran Covers Marie Claire China November 2022 Issue