The henley is a singular item, instantly recognizable, highly wearable, and simply classic and cool. No matter if you’ve owned a henley before or not, it’s an equalizer in the world of menswear. The best men’s henley shirts (including our picks below) channel the rugged sporting heritage from which the shirt originated, but now you’re more likely to find a henley worn with a cool-as-can-be denim shirt and slim black jeans at a rock show. Once you find the right henley — and once you realize all the ways you can wear your new favorite shirt — your wardrobe will never be the same. Consider this a serious upgrade to your casual style and waste no time in picking up this essential base layer.
Taylor Stitch Heavy Bag Henley
The right henley can be a gamechanger in terms of versatility. You can wear this Taylor Stitch henley (made with upcycled cotton) with everything from a classic blazer and faded blue jeans to a denim shirt and grey chinos (brown leather boots sold separately).
Flint and Tinder Raglan Waffle Henley
It’s the little things that make the difference when it comes to the design of a shirt, and the raglan sleeves on this American-made henley from Flint and Tinder offer one example. They’ll add some visual interest to any look when you rock this henley on its own. The rest of the time, the tough construction of this henley should make it a natural fit with a leather moto jacket and jeans.
Proof 72-Hour Merino Long-Sleeve Henley
When is it worth it to shell out nearly $100 on a henley? When that henley is made with antimicrobial fabric in a variety of colors and can be worn for days at a time.
Fjallraven Singi Merino Henley
The right henley can, as we’ve said before, function on its own as well as when layered up. Fjallraven has pioneered the perfect approach in that regard when it comes to the Singi Merino Henley, made with a durable-yet-breathable wool blend that makes it perfect to wear on the trail and back in town with a waxed trucker jacket.
Buck Mason Field-Spec Cotton Surplus Henley
Durability and dependability is the name of the game when it comes to Buck Mason’s gear across the board. Helpfully, this Field-Spec Henley, made with cotton jersey fabric and designed to call to mind old-school athletic shirting, carries on that lineage nicely.
Save Khaki Pointelle Henley
The perfect pairing alongside Save Khaki’s exceptionally perfect chinos? Why, the rugged-yet-wearable Pointelle Henley, a base layer that can be worn on its own or beneath a classic denim shirt with the brand’s impeccable pants. That’s what makes it one of the best men’s henleys.
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