The Best Henley Shirts to Ace Rugged Fall Layering

Best Men’s Henley Shirts

The Best Henley Shirts to Ace Rugged Fall Layering

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As the leaves start to turn and summer slowly but surely makes its way from center stage, there’s one rugged, go-anywhere shirt you should be wearing as often as possible: one of the best men’s henleys. The henley shirt is a valuable part of any well-dressed man’s wardrobe, but it’s especially indispensable come fall (and winter, too).

Think of it like a souped-up take on the long-sleeve shirt, with a more visually interesting two or three-button placket. The henley was initially designed as both a sporting shirt and an undershirt, but now, it’s stylish and cool enough to be worn on its own or layered underneath, say, one of the best denim jackets (to name but one other fall style pairing).

The button placket can help regulate air flow as temperatures rise and fall throughout the day, and there’s just something rugged and effortlessly cool about a henley (the collar can help frame your face, too). They’re a favorite of stylish celebrities, but the best men’s henleys can inject some of that same style into your own seasonal wardrobe.

You’ll find options both luxurious and affordable, each with something different to help amp up brisk fall style moves. Take it from us: these are the best henleys for men to shop now.

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Buck Mason Pima Curved Hem Henley

Buck Mason

The henley’s rugged workwear origins are the inspiration for Buck Mason’s near-perfect henley, fashioned from soft pima cotton with a pleasing texture. The curved hem flatters all body types, while the four-button placket is a cool, old-school touch that allows you to mix up how buttoned up you get. If you want to shake up your seasonal looks, try this one with a soft-shouldered herringbone blazer and inky blue denim.

$68 at

Ibex Travel Henley


Fall can throw any number of pursuits your way, from a morning coffee run to a brisk fall stroll to an afternoon spent knocking back an Oktoberfest beer or two. Rise to the occasion with a fabric that’s as versatile as your schedule: Merino wool, which wicks away moisture, resists odor and holds its shape through repeat wear. Luckily, Ibex crafted this durable henley out of the good stuff, and in a cool, goes-with-anything shade of dark olive.

$135 at

Wellen Brosnan Seawool Henley

Wellen Brosnan

Speaking of next-level fabrics, Wellen and the team at San Francisco retailer Huckberry have dreamed up some of the coolest material on the planet. Seawool is derived from material born of recycled plastic bottles and (get this) oyster shells, then turned into rugged and hard-working styles like this handy pocket henley. The rich Rojo color is a cool fall fashion move, while natural UV protection and temperature regulation bolster this stylish henley even further.

$78 at

Amazon Essentials Long-Sleeve Slim-Fit Henley Shirt

Amazon Essentials

It seems that no matter the menswear essential on your shopping list, Amazon Essentials has you covered — and at a highly affordable price, for good measure. This reliable henley shirt boasts a slim fit that’s flattering on its own and ideal for layering under chambray shirts or a quilted shirt jacket in equal measure. Plus, you’ve got your pick of eye-catching color combinations and a wide range of sizes — go ahead and pick up more than one.

From $6.17 at

Jockey Long Sleeve Waffle Henley

Jockey Long

There are going to be days this fall and winter where you’re going to have to ramp up your layering situation. Specifically, there are certainly going to be days where you’ll want to top off a waffle henley, like this one from Jockey, with a dependable flannel shirt. Jockey’s take on the henley is made from a polyester-cotton-spandex blend for stretch and mobility, and the bright white colorway pairs up with absolutely anything in your style rotation.

$34 at

Legendary Whitetails Slub Henley Shirt

Legendary Whitetails

The best henleys are meant for active pursuits, offering coverage, warmth and comfort all at once. Legendary Whitetails made its soft-washed slub cotton henley with those pursuits in mind, using a blend of cotton and polyester that should wear well with a waxed trucker jacket and canvas work pants for days in the field (or nights around the bonfire). The contrast stitching is a nice design detail, as is the four-button placket for visual interest.

From $14.63 at

Goodthreads Long-Sleeve Indigo Henley


Lean into the deep, rich tones of fall with an indigo henley in a seriously cool shade of blue. Add in stripes for good measure and then consider layering this affordably priced Goodthreads option beneath a light wash Western shirt for the ultimate in contrast and rugged good looks. The raglan sleeve detailing is also designed to flatter your chest and shoulders, never a bad style move to keep close at hand.

From $16.17 at

Fair Harbor SeaBreeze Henley

Fair Harbor

Searching for a henley to carry you from late summer into fall? Or a henley you can rock as a base layer on the beach or on a day hike? Fair Harbor’s aptly named SeaBreeze Henley can do a little bit of everything, thanks to a blend of recycled polyester, spandex and tencel, plus built-in UPF 50 sun protection. To top it all off, the entire garment is sustainably fashioned from using 14 upcycled plastic bottles. The Washed Red color is well-suited for fall style, as well.

$68 at

Carhartt Heavyweight Pocket Henley


The best men’s henleys on the market are designed to work as hard as you do, something Carhartt kept in mind when designing this hard-wearing henley. The cotton fabric is thick and heavier than average for layering protection in the cold, while the chest pocket is a useful touch you can put to good use for storage of everyday carry essentials. Add a Carhartt canvas jacket for good measure, then go forth and tackle fall outdoor projects with (relative) ease.

From $24.99 at

Eddie Bauer Ultrasoft Thermal Henley

Eddie Bauer

Eddie Bauer built its brand by putting its gear through rigorous testing in alpine conditions, and this henley should serve as a fitting, modern reminder of that dependability. The super-soft cotton blend in a thermal weave is geared to provide plenty of warmth as a base layer beneath, say, a denim overshirt or an Eddie Bauer puffer jacket, while the contrast placket is a visually appealing touch. For good measure, rib knit cuffs at the wrists ensure a snug fit in blustery weather.

From $55 at

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