Casually Tailored: The Henley Shirt

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Lately, I’ve been on a mission to find ways to dress down my tailored wardrobe. I tried wearing suits with sneakers, blazers with sneakers, and of course blazers with jeans!

All of them are great options to make a tailored outfit a little less formal, but this time around I wanted to incorporate one of my favorite shirts, the henley.

Casually Tailored In A Henley

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A henley is basically a collarless polo shirt with a placket at the bottom of a round neckline, and it usually has about 2–5 buttons.

It’s actually one of my favorite styles because they’re usually form fitting so that keeps me motivated to workout. I also really appreciate the placket because it provides more detail than just wearing a simple t-shirt.

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Even though the goal was to dress it down and make things less formal, I still preferred to tuck my shirt in. However, if the shirt was a little shorter and hit a few inches below the waistband it would have been fine to leave it untucked.

It’s one thing to dress down your outfit and make it more casual, but you can also run the risk of looking sloppy if it’s not done correctly.

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If you follow my Instagram, you already know that I plan on dressing a lot bolder for this upcoming fall/winter season. I’m talking about more plaids, windowpanes, and chalk stripe fabrics, and this plaid jacket (part of a suit) is just the first of many.

dapper-advisor-casually tailored-black-man-wearing-brown-trousers-tassel-loafers-1Jacket by Suit Supply, Shirt by Converse (similar), Trousers by Bureau (similar), Shoes by Zara (similar)

As always, thanks for reading!

Yours Truly,

Akil McLeod
The Dapper Advisor


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