The Best Henley Shirts to Upgrade Your Casual Outfits

two men wearing Henley shirts -
Courtesy of Cuts Clothing & Buck Mason
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If you’re a modern man, you’ve got to have a few henley shirts in your closet. Basically collarless polos, henley shirts make for great casual wear thanks to their simple design and a number of other practical reasons.

First, they’re almost always made from comfortable cotton that only gets softer over time. Second, they don’t have collars so there’s no pretending this shirt should be worn for anything too serious. Third, they make great stand-alone shirts, but they also layer well under sweaters and sweatshirts.

To that end, a lot of companies make lightweight and heavyweight versions of their henley shirts. And in the interest of further versatility, many companies also produce henley shirts with a waffle knit, which makes the fabric more breathable and more absorbent than traditionally knit henley shirts. Fourth and most importantly, in contrast to traditional crew neck T-shirts, henley shirts feature button-up plackets. That means no more squeezing your head through a too-small hole and stretching the head hole. The placket also gives you added flexibility in your personal style. You can button henley shirts all the way up for a tight clean look or leave them completely unbuttoned to show off a little chest for an easygoing look, not to mention increased airflow on those hotter days.

Put all this together and you can see why henley shirts have taken their place in men’s closets right alongside polos, crewnecks, V-necks and other collarless shirts as a classic fashion staple. They’re comfortable, versatile, generally come in a multitude of colors and easily pair well with khakis and jeans. That’s why we’ve picked out some of our favorite henley shirts below. We’re mostly focused on long-sleeve henley shirts here, but most of these brands make short-sleeve henley shirts too, in case you find an option you really love and want to stock up on the short-sleeve version.


1. Everlane Premium Weight Henley


Everlane got into the clothing business to make exceptional basics and the company delivered on that promise with its Premium Weight Henley. With this moderately priced shirt, you’re getting 6.2 ounces of high-quality cotton cut for the modern man in a trim, slim fit. The cotton is dense and the shirt is form-fitting without being too stiff, so it feels like it’s on the dressier side of henley shirts if you want to tuck it in and don a pair of nice shoes and blazer. But it also works as a great casual shirt for the weekend too with jeans, sneakers and rolled-up sleeves.  Add a solid three-button placket and the fact that the shirt comes in five go-to colors, and it’s hard to deny that this henley shirt just works for whatever you need, exactly what we’ve come to expect from Everlane.

best Henley shirts for men: Everlane premium weight henley shirt Courtesy of Everlane


2. Goodthreads Long-Sleeve Henley


For better or worse, Amazon is putting its money where its mouth is as it tries to enter the fashion marketplace. The company knows it can’t compete with pure fashion retailers, so instead, it focuses on producing bargain-priced staples with in-house brands. So it shouldn’t be a surprise that Amazon’s Goodthreads Long-Sleeve Henley was one of the cheapest henley shirts we could find. But just because Amazon can afford to offer a low price doesn’t mean it’s skimping on quality. This henley shirt, which comes in 12 colors at varying prices under $20, is made from surprisingly soft cotton with a three-button placket and a form-fitting but not tight regular cut. We generally prefer non-raglan sleeves (sleeves that do not run all the way to the collar and therefore don’t have separate shoulder seams) because we think the shoulder fit is generally better, but if done well, raglan sleeves more than get the job done. This is one shirt where raglan sleeves get the job done.

The only downsides here are somewhat cheap, loose cuffs and some shrinkage from washing. But as long as you’re OK with the former and factor in the latter, perhaps by sizing up and machine washing only on cold, you’re getting a solid henley shirt at a reasonable price with Goodthreads.

best Henley shirts for men: Amazon Goodthreads long-sleeve henley shirt in olive Courtesy of Amazon


3. PEGENO Fashion Casual Henley Shirt


Show off those muscles by keeping them covered with PEGENO’s front placket henley. It’s made from 95% cotton and 5% spandex, giving wearers a soft, moveable shirt with the right amount of stretch. It drapes on the body quite nicely and accentuates the male figure tremendously. This shirt is more or less the effortless throw-on type, making it a quick and easy way to look good in your day-to-day. The henley comes in a number of colors, but as it gets colder, this grey tone will have you fitting right in with the mundane weather ahead. Nobody wants to stand out too much when it’s cold outside.

best Henley shirts for men: PEGENO Fashion Casual Henley Shirt Courtesy of Amazon


4. Mack Weldon Tech Cashmere Henley


If you’re looking for a truly engineered, high-quality henley shirt, look no further than the Mack Weldon Tech Cashmere Henley shirt. Great on its own or as a base layer, this henley feels cut from the future with a modern trim fit that’s form-fitting without being clingy and a four-button placket, which is a bit less common. Besides the modern design, with excellent-fitting raglan sleeves, the real future twist is the fabric. The shirt is made of what Mack Weldon calls Tech Cashmere. The fabric consists of 47 percent modal, 38 percent Merino wool, 10 percent Cashmere wool and five percent spandex for 100 percent awesomeness.

Jokes aside, this fabric blend is no joke and offers a lot of benefits you simply can’t get from 100 percent cotton or wool. Modal is a kind of rayon fabric, but it’s stronger and softer than conventional rayon with the same resistance to shrinkage and ability to absorb more moisture. The use of Merino wool also helps wick moisture, keeping you dry and regulating your temperature, while also being odor resistant. Adding in Cashmere wool adds strength, lightness, softness and insulation. Then there’s the spandex, which gives the shirt increased flexibility and elasticity, meaning when you stretch the shirt, the fabric stretches with you and retains its shape much better over the long term.

Mack Weldon Tech Cashmere Henley shirt for men Courtesy of Mack Weldon


5. Carhartt Short Sleeved Workwear Pocket Henley Shirt


No matter how big, small, short or tall you are, this Carhartt pocket henley will fit. By giving us sizes from small to 4XL and a range of height options, just about any dude will have the ability to wear this comfortably. It’s made from 100% cotton with a durable chest pocket to keep items nearby for when you need them. This shirt is great for dudes that primarily work outside in cold weather because it’s created to keep the body warm and work well under pressure. There are a ton of colors to choose from, but there really is something special about this forest green color. It’s almost piercing, so we’re sure you’re going to turn some heads in this bad boy.



6. Taylor Stitch Heavy Bag Henley


If you don’t know Taylor Stitch, you’ve been missing out. The company makes staple men’s clothing built to last and designed with a distinct Americana flair. From leather jackets to boots and everything in between, these pieces will grow and age with you and most importantly never go out of style.

In keeping with its stated goal to build responsibly for the long haul, Taylor Stitch produced a three-button henley shirt designed to last with minimal environmental impact. (What can’t you do, Taylor Stitch?) The brand calls this the Heavy Bag Henley because it’s made of an eight-ounce upcycled cotton and recycled polyester, about 50-50 of each. The cotton-polyester combo makes this shirt dense and heavy but unbelievably soft for the weight, so it’s as durable and warming as it is comfortable. We tend to like tighter, slim-fit shirts, so we love this henley shirt, but if you like to roll up your sleeves or if you’re a more muscular gentleman, you might want to size up because the arms are tight and don’t have a lot of stretch in them. But that’s really the only downside we would identify.

Taylor stitch heavy bag henley shirt in natural color Courtesy of Taylor Stitch


7. Wrangler Plaid Woven Shirt


It’s getting chipper outside, to say the least. It’s time to layer up with one of our favorites from Wrangler. This relaxed fit henley is a comfortable staple to your casual selection of clothing and will keep you warm and cozy through fall and winter. It’s great to wear alone on warmer days as well as over your favorite undershirt to help keep the heat in when it gets colder outside. It’s textured with a waffle knit fabric that allows the shirt to be more wearable in colder temps, considering waffle is known for helping contain a bit of heat. Wear this baby to the bar, out shopping or at a bonfire with friends. Don’t love the black color? No worries, there are a ton more color options to choose from.

Wrangler Short Sleeve Plaid Woven Shirt for men (in black color) Courtesy of Amazon


8. Cuts Clothing Long-Sleeve Henley


If you need a modern, minimalist, no-frills henley shirt, Cuts Clothing has got you covered. Established in 2016, Cuts Clothing sought to make the cut of its clothes its raison d’etre and in so doing made shopping for your favorite kind of shirt as seamless as their well-crafted shirts. So if you like crew necks, V-necks, henleys, classic hems, split hems or elongated hems, you can easily shop for whatever category you want.’

The cut of this henley is just perfect to reduce any bunching, so you’ll never have that wrinkled-shirt look when you’ve been sitting down all day and get up to go out. Compared to some of our other favorite henley shirts, this henley runs fairly tight on the chest, shoulders and arms. But it’s got just the right amount of breathing room in the body so it’s not clinging too much to your skin. Though the shirt is pretty tight on the arms and upper body, Cut Clothing’s signature PYCA Pro fabric is breathable and super soft. We’ll admit it’s a bit of a turnoff that the brand doesn’t tell you exactly what goes into its signature fabric, but hey, the fabric delivers exactly what it says it does, so we’re not complaining.

Pick this shirt up in one of seven cool muted colors. For our pick, we really dig the henley in sage. It’s just the right level of muted green to differentiate yourself without standing out. And if you’re more of a split hem guy as opposed to a curve hem guy, the only difference between the shirts is the hem at the bottom, not to mention a few different color options for the split hem version.

cuts clothing long-sleeve henley shirt with curve hem in sage Courtesy of Cuts Clothing


9. Hanes Long-Sleeve Beefy Henley Shirt


Although we already talked about our go-to budget pick from Goodthreads, we couldn’t leave out this henley from Hanes. If you’ve ever owned anything from Hanes, whether it be an undershirt or a pair of boxers, you’ll know that these affordable garments go a long way. For just $9, this henley is a handsome, long-lasting henley that’s stylish enough to wear in public and never break the bank. There is a multitude of colors, too, so pick your poison and dress for less.

Hanes Men's Long Sleeve Beefy Henley Shirt


10. Ralph Lauren Indigo Jacquard-Knit Henley


The henley shirt originated as a rowing shirt in the city of Henley-on-Thames, England. It didn’t become a T-shirt alternative until designer Ralph Lauren popularized the design. Ralph Lauren still produces henley shirts today, including a snazzy Indigo Jacquard-Knit Henley with a three-button placket. The jacquard knit gives the shirt a cool woven texture, and the shirt is rinsed for a worn-in appearance and added softness. In terms of fit, this henley shirt comes in a standard, loose fit, so it’s not tight except for the ribbed cuffs. Be aware that Ralph Lauren uses actual indigo in the dying process, so color will rub off on to your other clothes, but that’s a small price to pay for the color of actual indigo and one heck of a stylish shirt. The real price you pay is the steep price of the shirt itself, which is definitely the biggest downside.

ralph lauren indigo jacquard knit henley shirt Courtesy of Ralph Lauren


11. Aimeilgot Cotton Linen Long Sleeve Henley Shirt


Add a pop of color to your winter wardrobe with this pink henley long-sleeve shirt from Aimeilgot. This baby is a wardrobe staple and will look awesome pair with jeans or khakis. It has a stylishly modern fit so you won’t feel too frumpy or squeezed inside and lightweight material so you won’t sweat if it gets a little toasty. This is the henley to wear from your transition from winter to spring, and while we’re still months away from that, it’s better to get on this trend early.

Aimeilgot Cotton Linen Long Sleeve Henley Shirt Courtesy of Amazon


12. Patagonia Long-Sleeve Work Henley


Henley shirts aren’t just for casual city fun. The right henley makes for great outdoor wear too, and few companies do outdoor better than Patagonia. The Patagonia Long-Sleeve Work Henley is made from a hefty 8.4-ounce blend of organic cotton and industrial hemp with a ribbed collar and cuffs as well as a handy chest pocket. The hemp helps make the shirt abrasion-resistant while the cotton keeps things soft. As is the case with all of Patagonia’s clothing in its Workwear line, the cut is pretty roomy so, between the cut and the three-button placket, breathability and airflow won’t be a problem.

In addition to literally feeling good and comfortable wearing this shirt, you can feel good knowing you’re supporting Fair Trade-Certified sewn clothing, too. As for our pick, we honestly like all four of Patagonia’s basic colors, but if you’re going hiking, blend into nature with the industrial green color. Just don’t get separated from your friends!

patagonia long-sleeved work henley shirt with pocket in industrial green Courtesy of Patagonia


13. Buck Mason Pima Curved Hem Henley


We’ve thrown a few heavyweight henley shirts your way, but you’re going to want something on the lighter side, too. The Buck Mason Pima Curved Hem Henley shirt is just what the doctor ordered. First, this shirt uses Pima cotton, an extra-long-staple cotton. The use of these longer cotton fibers results in a crazy soft fabric that’s stronger and more resistant to tearing, fading, wrinkling and pilling than upland cotton, the mass-produced cotton in most of our clothes. The use of Pima cotton alone makes this shirt a cut above the rest. But because Pima cotton is stronger than upland cotton, you can use less of it in a shirt, meaning you can ultimately have a lighter, equally durable shirt, which is exactly what Buck Mason has done.

A four-button placket, ribbed cuffs and a curved hem complete the package for a reliable, lightweight and comfortable henley shirt, available in two core colors and four seasonal colors.

Buck Mason Pima Curved Hem Henley Courtesy of Buck Mason


14. Mack Weldon Warmknit Waffle Henley


Yup, Mack Weldon made the list again for its excellent Warmknit Waffle Henley shirt. As we mentioned at the top, waffle knits are breathable and absorbent (which is why dish towels frequently have waffle knits), but waffle knits also provide extra insulation and warmth. This henley shirt makes good use of the waffle knit and it incorporates Thermolite, a heat-retaining insulating polyester, into the fabric blend for additional warmth. Combine that with modal, wool and spandex, a similar fabric blend to the Mack Weldon Tech Cashmere Henley, and you’ve got a henley shirt ready to greet fall and winter without breaking a sweat. For our color picks, we love the red fern color for fall and the charcoal heather for winter.

Mack Weldon Warmknit Waffle Henley shirt for men Courtesy of Mack Weldon


15. Flint and Tinder Supima Air Knit Henley


As promised, we’ve got a short-sleeve henley shirt favorite you need to know about with the Flint and Tinder Supima Air Knit Henley. Supima is just a brand to indicate the use of American-grown Pima cotton, so you can count on this shirt being soft, lightweight, unbelievably comfortable and it supports American growers. The fit runs slim for that form-fitting modern look without being too clingy on the body. The fabric, short sleeves and three-button placket allow for plenty of breathability to keep you cool on a hot day.

Of the four colors available, the dusty blue option is the most summer-ready right out of the box, but whichever color you get, you can’t go wrong with this great short-sleeve henley shirt.

flint and tinder supima air knit henley shirt for men in dusty blue Courtesy of Huckberry


16. Arc’teryx Sirrus Henley Shirt


For a shirt that looks good enough to wear on a date but has the moisture-wicking properties of a shirt that can handle a last-minute hiking session, we recommend the henley shirt from Arc’teryx Sirrus. Made with cotton, polyester and elastane, the Sirrus is a relaxed fit shirt that moves with the wearer. A great option for wearing around the home during cold months or outside during weekend adventures, the shirt features DryTech fabric that pulls moisture away from the body and keeps wearers cool even when they’re on the move. The extended length of the shirt makes it a great option for taller customers or anyone who is looking for more coverage. The Sirrus is finished with a three placket metal button closure.

Arc'teryx Sirrus Henley Shirt Courtesy of REI


17. Alternative Organic Long Sleeve Raglan Henley


For a classic henley style that is flattering and comfortable to wear, we like Urban Outfitters’ Alternative Organic Long Sleeve Raglan Henley. The long sleeve shirt is made from 100% organic cotton for a finish that is soft to the touch and washes up beautifully. Because the cotton is organically grown and processed, customers can also feel good knowing that the shirt they’re wearing was made in an environmentally friendly way without harmful chemicals that damage the soil and water supply. Saving the earth is always in style. The classically designed henley shirt is available in black, white and a light stone blue and is available in small to extra large.

Alternative Organic Long Sleeve Raglan Henley Courtesy of Urban Outfitters

18. PEARL iZUMi Coast Henley Bike Jersey


For those who feel the need for speed, they need a shirt that can keep up with all the miles they log on their bike. The PEARL iZUMi Coast Henley Bike Jersey is designed to move with the rider and keep them cool and comfortable no matter where they roll on two wheels. The polyester, cotton and TENCEL lyocell blend creates a shirt that is moisture-wicking and dries quickly. Designed specifically for cyclists, the shirt has angled shoulder seams for a fit that is conducive to reaching for handlebars. The hemline at the back of the shirt is also slightly shorter kit to make it more comfortable for riding. Reflective stitching and BioViz reflective elements throughout the shirt help to keep cyclists visible even when riding in the dark. The neckline is finished with a three-snap button placket for a classic henley look that also gives riders an alternative to the traditional zippered closure on bike shirts.

PEARL iZUMi Coast Henley Bike Jersey Courtesy of REI

19. BOSS Slim Fit Tipped Polo


For a henley that is appropriate for business casual situations thanks to its stylish and slim-cut design, we recommend the Slim Fit Tipped Polo from BOSS. The short-sleeve henley has several small details that separate it from its more casual peers. The two-button placket presents a finished look and the fit tip Polo collar creates added intrigue around the neckline. Slightly ribbed arm openings complete a dressy casual look. The 100% cotton henley has a soft and almost silky finish that makes this a great shirt to pair with jeans, khakis or even dress pants. The dark blue shirt is available up to 3XL.

BOSS Slim Fit Tipped Polo Courtesy of Bloomingdales

20. Under Armour Long Sleeve Performance Henley


Under Armour is a leader in performance wear and for good reason. The company offers a wide variety of clothing and accessories that move with the wearer and keep them cool even when working up a sweat. Under Armour is now making their long-sleeve performance shirt in a henley style, which gives customers the option to open a few buttons and get some ‘fresh air’ when working out. The classic fit, long sleeve performance shirt is moisture-wicking to help quickly pull sweat away and keep wearers dry and comfortable no matter what activity they’re doing.

Under Armour Long Sleeve Performance Henley Courtesy of Bloomingdales

21. Yarn Dye Stripe Henley by 1901


When most people think of henley shirts, they think of a long sleeve, solid-colored waffle shirt. But there is so much more to the wonderful world of henley. We like the Yarn Dye Stripe Henley by 1901, which has a casual feel and look to make it ideal for wearing around the house, to a party, or out for dinner with friends. The three-button half placket and crewneck style add to the casual feel of the henley, which has a slim fit for a more modern twist on the classic design. The tri-blend henley, which is made from cotton, polyester and rayon, is available in two heathered stripe patterns and can be worn on its own or as a layering piece during cooler months.

Yarn Dye Stripe Henley by 1901 Courtesy of Nordstrom

22. Patagonia Better Sweater Henley Pullover


Whether you are looking for a henley shirt that can be worn on its own or as a layering piece, has short or long sleeves, is solid or striped, most people would always prefer to opt for a piece of clothing that is gentle on the environment. That’s why we like the Patagonia Better Sweater Henley Pullover, which is made completely from recycled materials. The shirt is made from 100% recycled polyester fleece that has been dyed in an environmentally friendly manner that reduces the energy and water consumption of the conventional dying process. The fuzzy fleece interior of the sweater makes it comfortable to wear on its own or with a thin long sleeve shirt or undershirt. Made with Fair Trade Certified practices, the Patagonia Better Sweater can be worn as a warm single layer or paired with a vest or heavy outer shell. The versatile sweater can go from the office to the hiking trail and has a roomy fit that is still slim enough to make it stylish and appropriate for casual wear.

Patagonia Better Sweater Henley Pullover Courtesy of REI

23. Fjallraven Singi Merino Henley Shirt


Whether you are getting ready to hit the slopes, backpack through icy terrain or spend the day on a frozen pond working on your slapshot, the Fjallraven Singi Merino Henley Shirt is the best first layer of defense against cold weather. Made from traceable merino wool and durable nylon filament yarn, the shirt quickly wicks away sweat and insulates the user even when the fabric has become damp. This is crucial to clothes that are worn in cold weather since wetness can quickly lead to frostbite or hypothermia. Designed with flatlock seams to prevent chafing, the long-sleeved henley style shirt is also odor resistant thanks to its use of Merino wool.

Fjallraven Singi Merino Henley Shirt Courtesy of REI

24. Alternative Apparel Men’s Basic 3/4 Sleeve Raglan Henley Shirt


Pair two classics together for the ultimate in casual comfort with the Alternative Apparel Men’s Basic 3/4 Sleeve Raglan Henley Shirt. The baseball style henley shirt is available in four color combinations with contrast raglan sleeves. The relaxed shirt has a slight shirttail hemline with a merrow stitching detail for a more fitted finish than a traditional, looser fitting baseball shirt. The cotton, polyester and rayon blend come together for a shirt that has a slightly worn look that creates a vintage feel. The lightweight fabric makes it a great option for wearing during warmer months or layering when the temperatures begin to dip.

Alternative Apparel Men's Basic 3/4 Sleeve Raglan Henley Shirt Courtesy of Macys

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