For many, henleys can be a confusing garment. Not exactly loungewear, not exactly formal, it lies in the in-between sartorial space that isn’t easily defined. It’s slouchy but a bit fitted at the chest, with a bit of formality due to the top buttons at the collar. Either way, it’s a garment that, for many men, isn’t often explored properly.
Part of this may, in fact, be due to the history of the henley. It wasn’t meant to be worn outside the house. The henley’s ancestor were a pajama top and then, later, it became something akin to a workwear garment.
Today, the right henley can be one of the easiest garments to throw on and look put together. Instead of being confused by the buttons, embrace them. Keep your outfit as simple as possible and treat henley shirts like a clean palette to build an outfit around. I usually opt for a slimmer fit jean and may layer with a hoodie or jacket. I’ve even worn a henley as a shirt under a suit before, going as informal as I could get away with at a summer wedding last year.
Bonobos Jetsetter Performance Long Sleeve Henley
As classic as it gets, the henley from Bonobos is a breathable, casual top for every day wear. It’s made with 50 percent cotton and 50 percent DRYTEX fiber to wick away moisture, and it provides UV protection up to UPF 35 for those long days in the sun. It comes in both slim and standard sizing, so you can match it to your body shape.
Buck Mason Pima Short-Sleeve Hem Henley
Buck Mason has an unparalleled approach to reworking basics, and that extends to the brand’s short sleeve pima henley. The Supima cotton shirt comes in five colors: white, black, oat, heather gray, and a sage color that is dyed in a way to emphasize slight color variation for a vintage look. With the signature curved hem, the design team at Buck Mason has made a small, but noticeable, upgrade to the classic garment, making it feel new and classic all at once.
Mack Weldon Tech Cashmere Henley
With a blend of cashmere, merino wool, and modal, Mack Weldon’s henley is the perfect balance between performance apparel and luxury loungewear. Its heather gray color can easily be dressed up for date night or thrown on with a pair of shorts to hang around the house.
Ibex Travel Henley
Ibex’s 100 percent merino wool henley can easily transition between the seasons with you. The material is odor resistance and has a natural ability to regulate body temperature while wicking away moisture. It’s an ideal option to throw on for the airport or to layer over in the colder months, making it a great all-around staple for your wardrobe.
Todd Snyder Short Sleeve Jersey Henley
King of the classics, Todd Snyder showcases its inimitable approach to menswear basics with his jersey henley. With tailoring that go way beyond what’s “normal” for a short-sleeve henley and details like shell buttons, it’s the small things that make this a great option to add to your summer rotation. Or go for a few to mix it up–the six colors (white, black, navy, oil blue, gray, and pinecone) make it easy to fit the shirt to the occasion.
Sunspel x Paul Weller College Henley
Harkening back to vintage prep, Paul Weller and Sunspel have teamed up on perfect summer staple. This henley has contrasting ribbing around the edges with a two-button top, giving some Ivy sensibility without being overly customy. I’d pair this with a retro-inspired bathing suit for the ultimate boardwalk look.
J. Crew Garment-Dyed Slub Cotton Henley
Some garments you really want to live in without doing all the work of getting it loose and comfortable. J. Crew does the work for you with its slub cotton henley. A classic vintage ivory color with a not-too-thin cotton, it’s great for layer or as a stand-alone top for chilly evenings.
Hemen Biarritz Henley Harri
For classic European flair, look no further than Hemen Biarritz. Not as popular stateside, Hemen Biarritz makes garments that can last a lifetime with contemporary upgrades to classic fits. The Harri henley comes in 14 color options, and each features small detailing that really puts Hemen at the top of my shopping list.