How to Style a Henley Shirt: 8 Outfits for Men

The henley is the underrated middle ground between a t-shirt and a shirt. Its buttoned placket adds just enough detail to look considered without trying hard.

Choosing the right henley

• A slim or regular fit flatters most builds
• Cotton or a cotton blend is breathable and easy
• Long-sleeve henleys layer beautifully in cooler months
• Neutral colors are the most versatile, with one deep tone for depth

8 outfits

A henley with dark jeans and boots for a rugged look.

A henley under a denim jacket with chinos.

A henley with tailored trousers and clean sneakers.

A henley layered under a flannel or overshirt.

A henley with joggers and a bomber for a weekend feel.

The styling note

Leave the top button or two undone for a relaxed line, and tuck it in for a smarter take. The henley bridges the gap between casual and sharp better than any other shirt.

A good henley is the hardest-working shirt in a man's closet.