What To Wear With A Short-Sleeved Henley?

We love short-sleeved Henley tees. These collarless shirts with 2-5 buttons are an excellent way to switch things up and take a break from your regular crewnecks. 

Henleys are soft, comfy, and very versatile. They’re flattering to the body and are ideal when you want to show off what you’ve been doing at the gym! 

And while it’s pretty simple to style a Henley, some guys need advice about creating the best outfits. So what do you wear with a short-sleeved Henley? 

With a Jacket 

One of the easiest ways to wear short sleeve henley shirts for men is to pair them with a simple jacket. 

The choice of jackets is vast, but we recommend opting for something lightweight like denim, corduroy, or thin leather. However, you can always experiment with something warmer for colder days. We stan a bomber or utility jacket that will keep you warm and still look stylish. 

For the bottoms, choose jeans or chinos for casual every day and joggers or cargo pants for the weekends. 

With a Zipper Hoodie 

A Henley with a zipper hoodie and jeans is the ultimate weekend look. We love playing with some color: pair your navy Henley with an olive or maroon hoodie, or go for a monochrome look.

Henleys are mostly casual, but their neckline adds a little twist to even the simplest outfit, so you’ll never look dull!

With a Blazer

It might seem like we’re contradicting what we just said about casual style, but if done well, you can style a Henley with an unstructured office blazer too! 

An unstructured blazer is soft, deconstructed, and has minimum lining. Depending on the weather, choose wool, cotton, or linen fabric and pair the tee and the blazer with tailored jeans or chinos.

With a Patterned Shirt 

Whether you like classic checkered flannel button-down shirts or are into floral patterns, a plain Henley will be the perfect canvas for layering. 

As the tee will play a secondary role in the outfit, we recommend sticking to neutral colors such as grey, black, or white. 

This look is great for the weekend in the cabin (who doesn’t want to be a lumberjack at least for a day?), grabbing beers at your favorite pub, and if you’re opting for a floral shirt, it can be the perfect beach Holiday uniform!

With Slacks 

Yes, you can wear a Henley on its own paired with slacks. You can create pretty sleek looks with a good, stylish pair and a well-fitted tee. 

While this may not be an outfit for a gala dinner, it’s excellent for every day at the office or Friday night drinks. 

Don’t forget footwear, either. We suggest Derbys, loafers, Chukkas, or Oxfords.

Lastly, keep the colors subdued and go for the classic navy, black, grey, or maroon combinations. 

How To Wear It

Guys usually have a few questions when choosing and styling a Henley tee. 

First of all, what fabric should you choose? Opt for a thinner, lightweight Henley for spring and summer, and go for a thicker and heavier fabric for the cooler months. 

Next, do you tuck the tee in? There is no definitive answer because it depends on your style, preference, and outfit.

The good thing about Henleys is that they’re versatile, and you have a lot of free reigns here. When unclear, assess the shirt length; if it is too long (falls way below your belt line), you might want to tuck it all or the front in.

And what about the buttons? We recommend always keeping the top one or two buttons undone. 

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