blue henley with grey suit
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How to Wear a Henley (5 Amazing Outfits)

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The Henley is an incredibly underrated menswear staple.  Most men have closets full of t-shirts and polos but rarely a decent assortment of henleys. The henley is criminally underutilized. This article will not only show you how to wear a henley but also give you 5 amazing outfits to really look great in a Henley!

Are Henleys in Style in 2021?

Just like t-shirts, henleys are a classic menswear item. As such, they are timeless and always in style including in 2021! Moreover, unlike a t-shirt which most if not all men routinely wear, henleys are rarely worn which makes you stand out in a good way when you wear one.

5 Ways to Style a Henley

On Its Own

One of the best ways to wear a henley is by itself. The henley is a step above a t-shirt since the buttons on the henley add depth to an outfit. The key is to make sure the henley fits well since it is taking center stage. It should fit snugly in the chest and fall straight through the torso. Rolling up the sleeves is optional, but it looks so damn good with a henley, that you probably just should. Wear the henley with a pair of jeans or casual pants like I have done for a look that is casual but sharp. Adding desert boots and brown wayfarers just adds to this summer/spring look.

henley with chinos
Instagram: sharp.confident.man

Click here to find out How Chinos Should Fit.

Pairing the Henley with a Denim Jacket

The henley and the denim jacket are both rugged clothing items and as such pair seamlessly together. Keep the look simple with a black or dark grey pair of jeans for a look that is masculine yet refined. Just make sure the denim jacket and jeans have contrast. And then throw on a pair of your favorite boots and you have yourself a great look for early fall.

Want to get the perfect fitting denim jacket? Read ‘How a Denim Jacket Should Fit’.

Check out ‘How to Style Black Jeans’.

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Wearing the Henley with a Suit

I have seen many people style t-shirts under a suit so I thought why not try this look but with a henley. I think it looks better. Although a henley isn’t exactly a formal clothing item (like a dress shirt), it is still more dressy than a regular t-shirt. The buttons on a henley add dimension and contrast and helps you stand out from all the other men wearing simple t-shirts under a suit. This look is not intended as a replacement for formal attire but is a great way of dressing down a suit. I finished this look with a pair of vintage suede converse which gives the outfit a casual and retro feel.

Pairing the Henley with a Blazer and Sportcoat

If you’re not exactly ready to pair a henley with a full suit, then you could probably start off with a blazer/sportcoat. Sportcoats and blazers range in versatility depending upon the material and color so it’s best to start off with a blazer/sportcoat that leans more on the casual side like this burgundy blazer. Unlike a navy blazer which sits right under a suit on the formality scale, an unconstructed burgundy blazer can easily pair with more casual pieces such as a henley and dark wash jeans. This look is a great way to dress up a henley and a pair of jeans.

Want to get the perfect fitting blazer? Check out our Blazer Fit Guide!

Henley with a Field Jacket

Field jackets are incredibly practical and versatile. They pair well with both dressy and casual items. Here I took a dark green field jacket and paired it with a vintage henley and dark brown pinstripe wool pants. This outfit is a great blend of both casual and dressier pieces. The wool pinstripe pants add a dressy touch to the outfit, while the henley provides the rugged edge. The field jacket brings the look together by maintaining the rugged edge of the outfit but refining it ever so much alongside the dress pants. Pair this look with snow-ready winter boots for a great fall/winter look. 

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Should You Button a Henley?

For a 3 button henley, you should at least button 1 of the buttons. If you are wearing a 4 button henley, then you should button at least 2. If your henley has 5 buttons, then you should button 3 of them at least. Regardless of how many buttons your henley has, the most that you should unbutton is 2.

This prevents you from looking too stuffy where you have all the buttons buttoned and also too sloppy if you have all of them unbuttoned. I also find this compliments most body types.

How to Wear a Henley Sweater?

You can wear a henley sweater just like a normal henley shirt. Because henley sweaters are made from thicker and heavier fabrics, it is best to wear them in the fall and winter months underneath peacoats and topcoats. Wear henley sweaters with jeans, chinos and dress pants. Don’t wear anything underneath a henley sweater because they are not meant for layering like a crew neck or v-neck sweater.

A heavier henley is great in the fall and winter months. Pair them with dark wash jeans for a rugged look.

A heavier weight henley sweater is great in the fall and winter months. Wear them in place of a crew neck or cardigan sweater and you will definitely stand out.

This is a great smart-casual outfit. The henley gives this outfit a masculine edge.

Unlike a crew neck or v-neck sweater, you should not wear anything underneath a henley sweater. But you can always pair them with a topcoat, peacoat and other outerwear.

Conclusion

I hope you enjoyed this lookbook showing you how to wear a henley. In this lookbook I paired the henley shirt with both casual and sharp casual outfits to show you just how versatile this menswear staple is. Let me know what you think of the outfits and also how you like to style the henley shirt!

Lighter-weight options (great for summer/spring):

Heavy-weight options (great for fall/winter)