Black Shirt Jacket with Henley Shirt Outfits For Men In Their 20s

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White Henley Shirt Black Leather Shirt Jacket Black Chinos Black and White Canvas Low Top Sneakers

A black shirt jacket and a henley shirt paired together are a match made in heaven for those who prefer cool and casual styles. Add a laid-back vibe to by slipping into a pair of black and white canvas low top sneakers. This pairing demonstrates how to dress with style as you move through your 20s.

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Red Plaid Long Sleeve Shirt White Henley Shirt Black Leather Shirt Jacket Dark Brown Leather Watch Dark Brown Suede Belt Dark Brown Sunglasses Olive Jeans Dark Brown Suede Chelsea Boots

You'll be amazed at how easy it is for any gentleman to pull together this off-duty ensemble. Just a black shirt jacket and a henley shirt. Dress up your look with the help of dark brown suede chelsea boots. This is a combination you, as a guy in his 20s, can always rely on.

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Multi colored Plaid Long Sleeve Shirt Grey Henley Shirt Black Suede Belt Black Leather Shirt Jacket Black Sunglasses Brown Beaded Bracelet Olive Jeans Dark Brown Suede Chelsea Boots

This look with a black shirt jacket and a henley shirt isn't super hard to pull off and leaves room to more creative experimentation. Don't know how to round off this ensemble? Rock a pair of dark brown suede chelsea boots to amp it up a notch. As you're transitioning from your 20s to your 30s, you want to start dressing like a grown-up. In this case, combos like this become a great source of inspo.