How to Wear Henleys: An EveryMan's Ultimate Guide

Easy Upgrade, the Henley
When I was first starting out upgrading my wardrobe, I was obsessed with buying "dressy" clothing. I bought buttoned shirts, buttoned them all the way up and I did the same thing with polos, thinking that just having a shirt tucked in, buttoned all the way up and having a collar meant that I was "dressed up."
Looking back, this was an inherently limited state of mind, but there is nothing wrong with these looks. In fact when done correctly they can look quite nice:
Polos and dress shirts
Only if it is done right however. Even if you have the polo and buttoned shirt down, your wardrobe would be limited without the integration of a go between for these 2 options.That is why we will discuss how to wear a henley in the correct manner. 
Regarding the polo, while a great option during warmer weather, is lacking in functionality during cooler months due to the lack of long sleeves. The buttoned shirt is great in the office, but is restrictive in nature due to the material that most dress shirts are made of. In addition, buttoned shirts can only be dressed down so much. There will come a point where it looks "too dressy" and inappropriate. 
Take backpacking during the fall for example, you'll probably want to layer up for the cool evenings and at the same time want something that can be functional in such an environment. Right off the bat dress shirts do not fit the bill while polos are not the best layering option. 
Knowing this, some of you might go with the crew neck:
crew neck sweater
Its a solid option without a doubt, but I think you can do better! 
Its the subtle things in a man's outfit that can make all the difference. The one limiting factor of this piece of garment is the "crew" portion of the crew neck. The rounded portion of a crew neck does not serve to enhance the aesthetics of a mans chest. 
Let me put it another way, compare the next images. One is a sketch of a suit of armor from a thousand years ago, one is of a 3-piece suit:
V Taper
Do you notice the similarities? 
If you don't, here is the same image with some visual enhancements:
V Taper
For thousands of years, the "V-Taper" has been an inherently desirable male physique across cultures. The details inherent in such a body shape include:
  • Broad shoulders
  • Narrow waist
  • Wide Chest

I'm sure you'll agree that these are features that you would want. As a species it is what virtually all male members of the human race want because it signals:

  • Strength
  • Health
  • Vitality

We see this through clothing and armor throughout the ages. Our suit jackets usually have shoulder pads to build them up. This is the same with breast pockets, they puff up our chests. The suit jacket then has a button closure at the midsection that narrows our waist (visually).

Going back to the henley, it incorporates the same concepts of the suit jacket and armor.


Leaving 1 (or 2) buttons for a "V" to display on your chest. 

In addition, they are no more cumbersome to wear then a regular crew neck, simply leave one button unbuttoned at all times and it can be a pull over with no problem. Think of henleys as crew necks with an added feature. 
Henleys come in knit patterns for layering during colder months as well as in thinner fabrics for the Spring/Summer. The colors you choose are really up to you. But as a rule of thumb, darker colors (charcoal, navy, wine) work better for the Fall/Winter and lighter colors (light blue, white, light gray) are more suited for the Spring and Summer months. 
The Takeaway: For a go between piece that balances the casualness of the polo and the sleeves of a dress shirt, the henley is an excellent choice year round for casual occasions. They take the crew neck and make it better through adding a "V" to your chest that enhances your bodies masculine features.
Note: Leave at least one button buttoned, having it unbuttoned all the way down looks "slutty."
If your curious about the history behind the garment, check this out!

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