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Men’s Styling Guide – The Henley Look Book

The Henley Look Book

Since there are sooo many henleys looks, I am skipping the pleasantries and diving right in.

Look 1

A Henley as is with chinos or jeans and a pair of boots or sneakers.

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Look 2

A Henley worn under a long sleeve flannel shirts and a pair of jeans. Tuck the Henley in and leave the plaid unbuttoned. You may even add a belt if you wish. You can even roll up the sleeves a bit. If it’s cold outside add a beanie.

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Look 3

Mix things up a bit by picking a stripped Henley instead of a solid one.  Wear it with a pair of Chinos and sandals for a relaxed look or if you feel like dressing up a bit, then wear the striped Henley and chinos combo with a bomber jacket and substitute the sandals for boat shoes. Sunglasses will add some zing to your look.

Look 4

A base layer comprising of a Henley, with the middle layer being a denim jacket or vest and the final layer being that of a Bomber jacket.

Look 5

A Henley layered with a Gilet.

Look 6

You can add suspenders to this look and make it a really fresh and fun look.

Look 7

You can an extra layer between the DB Blazer and the Henley by wearing a dress shirt over the Henley. A cool idea would be to pick the Henley shirt and the double breasted blazer in solid tones and neutral hues and pick a funky shirt, maybe with polka dots or pinstripes or subtle prints in pastel or deeper tones. You can pick a plain shirt too if you are not sure of being able to pick the correct prints but still pick a nice shade for the shirt.


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