Henley shirts were always standing distinctive among other shirts and t-shirts. People who wore them, were always counted as a men, who have a sense in style and fashion. However, among all henley shirts, long sleeve henley shirts deserved the most part of attention.

Indeed, simple long sleeved t-shirts are not too dressy, polo long sleeve shirts are too neat. The last type of shirt left among long sleeves is henley shirt. And they fit that niche perfectly.

Long sleeve henley shirt is probably the best choice, if you are searching for a long sleeve t-shirt. So, lets discover best outfit ideas of them.

Basic Long Sleeve Henley Shirt Outfit


  • Top: light brown long sleeve henley shirt.
  • Bottom: black denim jeans.
  • Shoes: chukka boots.
  • Additional: brown leather bag.
  • Style Type: street.

No else words needed, just simple street outfit well suited for traveling or street walks.

White Long Sleeve Henley Shirt Outfit


  • Top: white 3/4 pushed up sleeves henley shirt.
  • Bottom: blue jeans.
  • Shoes: might be white sneakers (suits best here).
  • Additional: black leather jacket.
  • Style Type: street.

The most popular (and my favorite) combo of light blue jeans + white t-shirt also can take place here. In fact, this look with henley shirt is somewhat better than simple white t-shirt.

Black Henley 3 Button Shirt


  • Top: black 3/4 pushed up sleeves henley shirt.
  • Bottom: blue jeans.
  • Shoes: chukka boots or oxfords (would be nice here).
  • Style Type: semi-casual street.

Although it is a shirt, actually it is very close to sweatshirt. That fact make that look a little bit dressier than usual street style. That’s why it is called semi-casual street. More info about style types read in the article dress codes for men.

Bicolor Long Sleeve Henley Shirt


  • Top: bicolor henley shirt.
  • Bottom: grey chinos.

No else words needed, as you see from the picture, this henley has white under lay, which is the main feature of that shirt.

Henley + T-shirt Underwear Combo


  • Top: blue 3/4 pushed up sleeves henley shirt, v-neck navy blue t-shirt
  • Bottom: white chinos.
  • Shoes: fashion loafers.
  • Style Type: casual.

Neat Dressy Casual Outfit with Henley Shirt


  • Top: white long sleeve henley shirt (short sleeves also acceptable here), white casual blazer
  • Bottom: jeans.
  • Shoes: fashion sneakers.
  • Style Type: neat-dressy casual.

This look wouldn’t be as great if it were simple t-shirt or white shirt.

Simple t-shirt is bringing too much street style and it would be a complete mess here, cause when you put on casual blazer you want to look dressy and neat. But when you put on simple white t-shirt you completely ruin such look by adding some dose of street style, what is unacceptable here.

By the way, white shirt is also bad here, cause it doesn’t suit with jeans. Shirt + jeans is good in smart style, but not in the neat-dressy casual.

Vintage Long Sleeve Henley Shirt Style


  • Top: white long sleeve henley shirt.
  • Bottom: rolled up jeans with suspenders.
  • Shoes: brown oxfords.
  • Style Type: vintage.

Basically, henley shirt is not a common type of wear like shirt or t-shirt. So, if you want to create a cool vintage style, which you can use in real life, then henley shirts are the best top wear to choose.

Although it is a vintage style, it doesn’t look like “wear only at exhibition or a thematic party”


As we seen, henley shirts are well suited for casual looks. They can be used to diversify your wardrobe and renew appearance. So, if you are on mind to buy some, do it now and think about a whole outfit, rather then a single henley.


Written by Renato Varran