14 Best Men’s Casual Henley Shirts for Perfect Layering

How long do you think your henley shirt can last? Can it withstand repeat wear across a grueling three-day weekend? Huckberry seems to think so, as its Proof line blends the best of rugged workwear with reliable modern fabrics.

Huckberry even says they’ve taken the shirt around the world without missing a beat, and in my experience, the merino fabric performs wonderfully. It retains its shape, it wicks away moisture, it looks polished and it comes in a wide range of colors for day-to-night style.

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.

I’ve found that the fabric is sturdy without being overwhelming, and surprisingly supple – the cuffs and waist hem tend to bounce back after a long day’s wear, and the color never seems to fade. Of course, its Heavy Bag fabric is also eco-friendly.

The San Francisco company’s blend of upcycled cotton and recycled polyester is both sustainable and substantial without overdoing it, with a sturdy hand feel ideal for teaming with other Taylor Stitch essentials (try it with a waxed field jacket or shawl cardigan).

Some of the best men’s henleys, in my experience, are suited for rugged leisure, and others are made to get down and dirty through rough-and-tumble seasonal work in the yard.

I’ve found that Carhartt falls nicely into that second category, especially the burly heavyweight construction of this essential seasonal fit. It gets even better when worn underneath a Carhartt work jacket.

Bonobos made its Jetsetter line for the guy on the go, focused on stretch, comfort and crisp style from coast to coast. This henley lives up to the name, and then some.

While some henleys are made from thick waffle fabric for insulation, this piece uses a blend of soft pima cotton and moisture-wicking DRYTEK material for a breezy feel. Take your pick from Slim or Standard fits in a range of sizes, and consider picking up multiple colors to round out a globetrotting wardrobe.

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.

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 first made waves as an ideal gear pick to wear for a day on the water, be it fly fishing or a day out on the deep sea (which is how I first discovered the brand). Its fabric both protects you from the sun and keeps you cool (even its long-sleeve pieces). This durable henley is well-suited for dry land in particular, perhaps as you grab a cold beer after a day in the sun.

I’ve found the brand to be particularly useful as a base layer on day hikes, and yet the collar and overall design stands up to more casual pursuits beneath my trusty waxed trucker jacket.

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.

The design of a henley, on the surface, can’t be changed much. There’s the front button placket to provide more coverage or ventilation, and there are touches like ribbed wrist cuffs for a secure fit.

Buck Mason went a couple steps further, first in its use of soft, breathable pima cotton, and then with the use of a curved hem that flatters the body. They weren’t the first brand to revamp the henley, but they might be the most beloved, and this henley is exhibit A. It’s especially flattering with the brand’s shawl cardigan or its perfectly faded jeans.

If any brand knows the benefits of an ultra-warm, dependable base layer, it’s Filson. The company’s Pacific Northwest heritage shines through to this day, with gear and designs that refuse to take no for an answer.

Dependable 12oz. Waffle-knit cotton offers an extra shot of insulation on frigid mornings, while the two-button extended collar is a heritage design detail. Wear this one to stoke the fire on a brisk cabin morning, or use it as a base layer for an early-morning day in the field – it won’t let you down.

Sometimes, you need a henley with a beefier, tougher build, even moreso than the best henley shirts on the market.

Take the Outerknown Big Heavy Tee Henley, which steps things up considerably in terms of weight and construction. The key is the use of certified organic heavyweight cotton jersey, all the better to bolster all your fall ‘fits.

Durable waffle-weave fabric adds texture and utility to many a fall #OOTD, at least in my experience, and Wrangler makes a classic, affordable option that pairs supremely well with its iconic trucker jackets and shirt jackets.

It functions as readily on its own, of course, especially with expertly cut Wrangler jeans.

With its sporting roots as worn by rowers in Henley-on-Thames, the henley might be the ultimate performance shirt – it’s a clear home run in Vuori’s lightweight, moisture-wicking performance fabric.

Use the button placket to customize your fit and ventilation when training, or opt for it as off-duty loungewear in an array of cool colors.

The best henley shirts are a crucial base layer out in the field, and Patagonia knows this better than anyone.

Ultra-soft 100 percent organic cotton makes the difference in terms of sustainability, while the rib-knit neckline and contrasting three-button placket deliver a secure fit and subtle style points in brisk weather, on and off the trail.

There’s a difference you can feel right away when wearing Reigning Champ menswear – its fabric is sturdy and strong yet supple, from T-shirts to tank tops to one of my favorite henley shirts.

The design might seem simple on the surface, but the results in matters of comfort, utility and even minimal style speak for themselves – it’s one of the best henleys for men you can buy, no doubt.