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The Best Casual Henley Shirts for Men in 2023
By Beau Hayhoe | Updated February 27, 2023
Courtesy of Taylor Stitch
The best men’s style essentials do more than what’s expected of them, and they perform in a reliable manner just about all the time. Take the humble, hard-working henley. When done the right way, in durable, high-quality fabric, it can function as a base layer–or the centerpiece of multiple outfits.
You can dress it up just a touch, or wear it dressed down with jogger pants. You can throw one on underneath a shirt jacket or a trucker jacket–or a soft-shouldered wool blazer. The best ones even flatter your body and add a dash of rugged appeal on the daily.
WHAT YOU SHOULD KNOW
- All in a name: The henley takes its name from Henley-on-Thames, where early styles were used as a sporting layer by British rowers who needed a dependable shirt.
- Utility and style in one: The three or four-button henley placket offers either extra coverage or added ventilation, plus a visually appealing style touch beyond a plain crewneck.
- Functionally minded fabric: The best henleys are made from all sorts of fabrics, ranging from moisture-wicking merino wool to soft cotton and warm thermal waffle knits.
- Flattering fit: The henley has a rugged and rough-and-tumble appeal that looks good on every guy, especially layered with a flannel or chambray shirt.
What is a Henley shirt?
Think of the henley, with a three or four-button front placket and long sleeves for extra fall and winter coverage, as the multi-tool of your wardrobe.
Some are made of fabric like breathable merino, others use thick-knit waffle construction, and still others incorporate organic cotton into the mix–there’s not really a wrong way to go with one of the best men’s henleys.
It’s the kind of piece every guy could stand to wear more often, especially as you look for casual-yet-useful pieces for colder weather.
Our favorite henleys stand the test of time, thanks to dependable construction, cool colors and comfortable fabrics, to name but a few stellar attributes. To learn about some quality men’s henleys, all you need to do is keep scrolling through our top selections.
James Perse High Twist Recycled Jersey Henley
$175
When you obsess about quality fabric and cool silhouettes, the rest tends to just fall into place, as with this recycled cotton jersey henley from James Perse.
The lightweight cotton fabric makes this an ideal layering pick beneath a rugged denim shirt or a thick-knit cardigan, but touches like side split stitching make it edgy and eye-catching enough to wear on its own with olive chinos before temperatures really plummet. It’s a classed-up basic that’s not so basic after all, and your investment will surely pay off.
Taylor Stitch Heavy Bag Henley
$68
Perhaps it’s the way the button placket of a henley frames your face, or perhaps it’s the crisp appeal of the deep Navy colorway, but all the proper details come together quite handsomely with this near-perfect Taylor Stitch take on the henley.
The San Francisco company’s blend of upcycled cotton and recycled polyester is both sustainable and substantial without proving too stifling, with a sturdy hand feel ideal for teaming with other Taylor Stitch essentials (try it with a waxed field jacket or shawl cardigan).
Everlane Waffle Long-Sleeve Henley Tee
$60
Remember what we said about the best men’s henleys coming in all shapes and sizes, so to speak? Well, here’s a soft organic cotton option if minimal, eco-conscious style is your main priority.
Especially in sleek Black, it’s the kind of henley to pair with other subtle fashion choices, like a black moto jacket and grey jeans (don’t forget black moto boots, of course).
Sometimes, straightforward style is the name of the game, and Everlane’s no-frills designs – particularly one of the best men’s henleys – check all the right boxes.
L.L. Bean Carefree Unshrinkable Henley
$35
It’s a beautiful thing when you can trust a flagship brand to do more than one thing exceptionally well, as with L.L. Bean and its penchant for crafting outstanding cold-weather classics in multiple categories.
For less than $35, you’d do very well to pick up at least one well-made L.L. Bean henley, developed from soft jersey-knit cotton that won’t shrink or fade over time.
An astounding 12 color options give you plenty of choices no matter your style preference, while sizing options (Regular or Tall) offer something for everybody, too.
Free Fly Bamboo Flex Henley
$74
Free Fly definitely knocks it out of the park when it comes to fabric, using a flexible blend of bamboo fibers for warming insulation and temperature regulation in equal measure.
Colors like Heather Black wear well with shades of navy, grey, olive, maroon … you name it, and the right henley can get the job done.
AETHER Apparel Japanese Merino Henley
$225
AETHER Apparel was founded at the cutting edge of sleek, city-ready style and off-trail functionality, which is why its merino henley is one of our favorites. Merino is a natural performance fabric, made to resist odor and provide breathable moisture-wicking capability all the while.
It’s durable yet soft, able to be layered beneath a denim jacket or a cozy flannel shirt, and best of all, built to last. AETHER’s option checks all the right boxes and looks stylish all the while, especially in a classic Bone or Navy color.
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