Frequently Asked Questions
What is a Henley shirt?
A men's Henley shirt is a type of casual shirt that typically has a round neckline with a buttoned placket, similar to a polo shirt. Heritage labels like Sunspel, John Smedley, and others featured in our old money brands guide make some of the best Henleys you can buy.
It is typically made of comfortable and breathable fabrics and it can be either short-sleeved or long-sleeved.
It's known for its versatility and can be worn as a standalone shirt or layered under jackets or sweaters.
Why is it called a 'Henley' shirt?
This shirt is named after the town of Henley-on-Thames in Oxfordshire, England.
Originally worn by the participants in the Henley Royal Regatta, it gained popularity among rowers and eventually became a fashionable item of clothing worn by both men and women.
Are Henley shirts suitable for different body types?
No! Learn more in my 'Who Can Wear Henley Shirts?' section below.
Can men wear Henley shirts for dressier occasions?
Also, no! Henleys are a casual item only.
What are the different styles and variations of men's Henley shirts?
The classic Henley shirt typically features a round neckline with a button-up placket, long sleeves, and a straight or slightly curved hemline. However, there are also short-sleeved Henley shirts available for warmer weather.
In terms of variations, you can find Henley shirts in various fabrics such as cotton, linen, or even blends with synthetic materials.
How do I layer a Henley shirt?
Like your t-shirts, a Henley works best as your base layer. That said you could wear it over an undershirt or thin t-shirt, provided that you can't see the outline underneath the Henley.
A Henley looks best by itself, but you could always wear it under a jacket, blazer, or an overshirt if you want some extra insulation.
Are Henley shirts in style in 2026?
Yes — Henleys remain a wardrobe staple in 2026. Their versatility as a layering piece and standalone casual top keeps them relevant season after season. The buttoned placket adds visual interest that a plain t-shirt can't match, making them a go-to for smart casual and casual settings.
Can you wear a Henley to work?
Only in casual work environments where t-shirts are also acceptable. Henleys are a casual item — they don't meet business casual standards. In creative or tech workplaces with relaxed dress codes, a clean, well-constructed henley in a neutral color works. For anything requiring a collar, opt for a polo instead.
What do you wear under a Henley shirt?
Ideally, nothing — or a thin, invisible undershirt. The Henley's neckline and placket are designed to be seen. A visible crew-neck tee underneath defeats the purpose. If you need a layer underneath for warmth, choose a V-neck undershirt that sits below the Henley's neckline.
Are Henleys still in style?
Yes. The Henley shirt has been a wardrobe staple for over a century and remains current in 2026. Its blend of casual ease and visual interest (thanks to the placket) keeps it relevant year after year. Stick to neutral colors and quality fabrics and you'll get years out of every Henley you own.
Henley vs t-shirt vs polo — what's the difference?
A t-shirt is the most casual: round neck, no buttons, no collar. A Henley adds a buttoned placket — slightly more interesting, still casual. A polo adds a collar and is the most versatile of the three — it's the only one that works in business casual settings. Use t-shirts for the most relaxed looks, Henleys for casual with a bit more character, polos when you need to look slightly polished.
Henley Shirts Mistakes Most Men Make
Despite its relatively plain aesthetic, the Henley shirt can be tricky to pull off. Here are the most common mistakes you want to avoid:
- Wearing Henleys with bold colors or loud patterns.
These never look good. If in doubt, stick to dark neutral shades, as these are the most versatile and stylish options.
- Wearing for non-casual dress codes.
Henleys are casual shirts and work only in casual outfits.
- Wearing a Henley if you don't have the body for it.
This is a big no-no. Learn more in my 'Who Can Wear Henley Shirts?' section below.
Colors
Like your sweaters and t-shirts, I'd recommend sticking with neutral-colored Henley unless you really know what you're doing.
Some of my favorite shades are black, navy, and charcoal.
Fabrics
Generally, Henleys will be made out of cotton, so there's really not much choice outside of that, but you still need to consider fabric weights depending on the time of year.
The main thing to know is that lighter weights should be worn in warm weather. Thicker, heavier fabrics in cooler weather.
You can get them in everything from a lightweight summer weave, where it feels like a t-shirt, to thicker, quilted versions which will keep you warm during the cooler months.
You don't have to worry too much when buying them because, based on the time of year, most brands will carry the appropriate weights. But I still want you to be aware of it just in case.
Different Types Of Henley Shirts
Short-Sleeve Henleys
A short-sleeve Henley is similar to a polo shirt but it hasn't got a collar and it usually has a more relaxed fit.
Wear your short-sleeve Henley as you would a crewneck t-shirt. The two are interchangeable in the same outfits and can be worn on their own or underneath a jacket.
Long-Sleeve Henleys
In my opinion, long-sleeve Henleys look better than short-sleeve ones and they're a great go-to item when you're looking for something between a polo or a crewneck t-shirt and a sweater.
During the warmer months you can wear them with the sleeves pushed up. Trust me, women love to see sleeves rolled/pushed up around your forearms.
However, I mentioned earlier that Henleys aren't for everyone...
Who Can Wear Henley Shirts?
Whether you can wear a Henley or not depends solely on your body type, and I hate to say it, but not everyone can wear one.
Slim Build
If you're a thin guy, no matter your height, if you want to wear a Henley, you need to nail the fit, especially if you're going to wear a long-sleeved version. If the fit is too loose, it'll make you look thinner and more frail than you are – not good!
A long-sleeve Henley on thinner men works if they're layered underneath a jacket, like the below-right image. When worn on their own, it really spotlights and elongates your thinner torso, slimmer arms and neck, like the image on the left. So if you're a thinner guy and want to wear a Henley on its own, then wear a short sleeve version since it'll look similar to a t-shirt.
Athletic Build
I personally think that Henleys look best when worn by guys with a muscular athletic build. Exhibit A:
The reason why is that the Henley was originally designed as an under-layer rather than an outer one. As a result, they have a really trim fit across your body, particularly throughout your shoulders and arms which can look really sexy if you're in shape but...
Larger Build
If you're a rotund gentleman (aka you have a belly - this includes dad-bods), you shouldn't wear a Henley shirt, period.
Allow me to show you why and explain. See Exhibit B:
Because of the button placket on the front, coupled with the lack of a collar, a Henley will shine a massive spotlight on your bigger torso.
This is when a polo shirt is perfect and should be used instead because a polo shirt's collar will visually keep your torso balanced and in proportion, so your top half doesn't look so big compared to your bottom half. The image below of James Corden shows a guy with the exact same body type as the image above but in a polo shirt. Talk about a night and day difference…
How To Wear A Henley Shirt
Like all your clothing, including Henleys, they should have a trim fit throughout the body and arms – no matter your body type. You never want it to be too loose anywhere because that's when you'll look sloppy and not put together. You shouldn't be able to pinch more than 1-2 inches of fabric on one side of your belly button and no more than an inch around the bicep.
The image below highlights the proper fit around the torso and sleeves.
Outfit Ideas
Like I've already said (multiple times), the Henley should be thought of as a casual item and worn in certain ways, depending on your body type (or not at all).
Here are a few of my favorite ways to wear a henley shirt.
As Mr. Reynolds has an athletic/muscular physique, he can get away with wearing his henley on its own.
Henleys work great as a layering piece during colder months and here we have one layered under a stylish olive work shirt.
In case you haven't guessed by now, charcoal is a super versatile color for Henley shirts. See how we've layered it under the bomber and tucked it into the front of our jeans to show off our belt and earn some bonus style points.
Mens Henley Shirts: Complete Style Guide
Mens Henley shirts sit in the sweet spot between a t-shirt and a polo — more interesting than the first, more relaxed than the second. They've been a menswear staple since the 1800s and they're not going anywhere.
The four things that make a great mens Henley shirt:
- Placket length — typically 3-4 buttons. Longer plackets read more casual; shorter ones look cleaner.
- Neckline — a clean, reinforced collar that sits flat. Avoid flimsy or stretched-out necks.
- Fabric weight — light cotton for warm weather, waffle knit or thermal for cold. Heavier knits drape better.
- Color — dark neutrals (black, navy, charcoal, olive) carry the look. Save lighter colors for athletic-built guys.
How to build a Henley shirt collection:
- First Henley: Long-sleeve charcoal or black, mid-weight cotton.
- Second: Short-sleeve navy in lighter weight for warmer months.
- Third: Waffle-knit or thermal in oatmeal or olive for layering under jackets in fall/winter.
What separates a good Henley from a bad one: Construction quality. Cheap Henleys lose their placket shape after a few washes — buttons sag, the neckline stretches, and the placket curls. Spend slightly more for a Henley with reinforced stitching at the placket and a structured neckline.
Henley Outfit Ideas for Men
Five Henley outfit formulas that work across casual settings:
1. The Solo Henley
Charcoal long-sleeve Henley + dark indigo jeans + brown leather chukka boots. The simplest, most reliable Henley outfit. Roll the sleeves to the forearm.
2. The Layered Henley
Black Henley + olive overshirt or chore coat + black jeans + brown suede boots. Adds depth for cooler weather without bulking up.
3. The Henley + Blazer
Navy Henley + unstructured navy blazer + grey wool trousers + brown loafers. The "smart casual" Henley combination — works for relaxed creative offices and date nights.
4. The Henley + Bomber
Oatmeal waffle Henley + olive bomber jacket + dark wash jeans + white sneakers. A modern casual layered look.
5. The Short-Sleeve Summer Henley
Navy short-sleeve Henley + stone chinos + brown leather loafers + sunglasses. The warm-weather Henley outfit. Tuck the front of the shirt loosely for a relaxed silhouette.
Common rule: Keep the rest of the outfit simple — Henleys do the visual work on their own. No bold patterns, no statement accessories.