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