Written by Ben Chuang

 

Introduction to the Henley Shirt

The Henley shirt is a staple in men’s fashion, bridging the gap between a basic T-shirt and a more structured type of shirt.

It offers a stylish, versatile look that suits various settings. Its unique buttoned placket adds an element of sophistication while maintaining a casual feel.

Unlike standard T-shirts, Henleys provide a more tailored look, making them a great choice for a wide range of occasions. But what is a Henley shirt, and how does it stand out in the world of menswear?

This guide will take you through its history, key features, materials, styling tips, and the best brands to consider.

A Brief History of the Henley Shirt

The Henley shirt traces its roots to England, where it was originally worn as an undergarment in the 19th century. It gained popularity as a rowing uniform in the town of Henley on Thames, which inspired its name.

The reason it was favored by rowers was its breathability and ease of movement, providing better comfort than a fully buttoned or collared shirt.

Over time, the Henley evolved from being an athlete’s choice to a fashion staple. In the 1970s, designers introduced Henleys to mainstream fashion, and today, they are a wardrobe essential for men and even women who appreciate their stylish, rugged appeal.

 

Key Features of a Henley Shirt

If you're wondering what is a Henley shirt, they're characterized by their collarless design and a placket with two to five buttons.

They come in short and long sleeves, making them a versatile choice for different seasons. The lack of a collar gives Henleys a casual outfit aesthetic, while the buttoned neckline adds structure and style.

Some Henleys also feature ribbed cuffs, contrast stitching, or textured fabrics that enhance their overall appeal. The combination of form and function makes Henleys a smart casual choice for those who want something more stylish than a T-shirt, but not as formal as a polo or slim fit dress shirt.

Difference Between a Henley and a T-Shirt

While Henleys and T-shirts are casual, the Henley shirt definition features a round neckline and buttoned placket, setting it apart from a standard crew or V-neck T-shirt.

This simple detail of the Henley neckline adds sophistication and makes it a better transitional piece for casual and semi-formal settings.

Additionally, the Henley neckline has a more structured fit, making it a flattering option for a wide range of body types. The buttoned neckline also provides the option to adjust for comfort, allowing wearers to style them according to their preference.

 

Difference Between a Henley and a Polo Shirt

Henleys and polo shirts have buttoned plackets, but the key distinction is the collar. A polo shirt features a fold-down collar, giving it a slightly more formal appeal, while a Henley sports a round neckline for a more rugged, laid-back look.

Polos are often made from cotton or blends that provide a sporty feel, while Henleys are more commonly made from soft, breathable fabrics.

While polos are associated with preppy or golf attire, Henleys have a more casual, masculine appeal, often associated with outdoor activities and vintage workwear.

Feature	Henley Shirt	Polo Shirt
Collar	No collar, round neckline	Has a soft, fold-down collar
Buttons	Button placket (usually 2-5 buttons)	Button placket (usually 2-3 buttons)
Sleeves	Short or long sleeves	Mostly short sleeves (some long sleeve versions)
Material	Cotton, waffle-knit, or thermal fabrics	Cotton, pique, or jersey knit
Fit	Casual and slightly relaxed fit	More structured, semi-formal fit
Style	Rugged, laid-back	Preppy, smart-casual
Best For	Layering, casual everyday wear	Business casual, golf, semi-formal settings
Origins	19th-century British rowers	Tennis and golf sportswear
Versatility	Works as a base layer or standalone	Typically worn as a standalone piece

 

Common Fabrics Used for Henley Shirts

Henley shirts come in various fabrics to suit different occasions and weather conditions. Common materials include:

• Cotton: Soft, breathable, and ideal for casual wear. Pure cotton Henleys offer comfort and durability, making them a staple for everyday outfits.

• Waffle-knit cotton: Provides warmth and texture, perfect for layering in fall and winter outfits for men. The waffle shirt weave adds a unique touch that makes Henleys stand out.

• Linen: Lightweight and airy, great for summer outfits for men. Linen Henleys provide excellent breathability and moisture-wicking properties.

• Blends (Cotton-Polyester, Cotton-Spandex): Polyester offers stretch, durability, and moisture-wicking properties. These blends are excellent for those who prefer Henleys with added flexibility and performance features.

 

Long-Sleeve vs. Short-Sleeve Henleys

Long-sleeve Henleys (or even a Henley sweater) are excellent for layering and provide warmth, making them ideal for fall and winter outfits.

They are commonly worn under jackets, vests, or even flannel shirts for a rustic, layered look. Short sleeves, on the other hand, function similarly to T-shirts and work well for summer outfits.

They offer a breathable, stylish alternative to regular crewneck tees. Choosing between the two depends on seasonality and styling preference, but both versions provide a smart, polished alternative to basic shirts.

 

Best Henley Shirts

If you're looking to buy Henley shirts, you're in luck, as I've done some research to compile some of the best Henley shirts available on Amazon, with options for both long and short sleeves. Some of the best brands for men's Henley shirts include:

True Classic Long Sleeve Henley

The True Classic Long Sleeve Henley is designed for those who appreciate a perfect balance of comfort and style. Made from a premium cotton-polyester blend, this Henley offers a soft, lightweight feel with just the right amount of stretch for a flattering fit.

The athletic cut contours the body without feeling too tight, making it ideal for layering or wearing solo. Its three-button placket adds a touch of versatility, allowing for an adjustable neckline. Whether dressed up with chino pants or paired with denim, this Henley delivers everyday wearability with a refined, modern aesthetic.

Lucky Brand Venice Burnout Henley

The Lucky Brand Venice Burnout Henley brings a vintage-inspired look to a classic casual shirt. Designed with a unique burnout fabric, it has a slightly faded, lived-in feel that exudes effortless cool. Made from a cotton-modal blend, it’s ultra-soft, lightweight, and breathable, making it an excellent year-round option.

The tapered fit and subtle ribbed cuffs enhance its modern appeal, while the three-button placket keeps the style versatile. Whether paired with jeans for a laid-back weekend look or layered under a jacket for added warmth, this Henley provides a stylish, easygoing aesthetic that complements any outfit.

Sailwind Long Sleeve Henley T-Shirt

For those seeking a soft, lightweight Henley, the Sailwind Long Sleeve Henley T-Shirt is a standout choice. Crafted from a premium cotton blend, it offers a breathable, slightly stretchy feel for all-day comfort. The slim-fit design provides a modern silhouette, making it easy to dress up or down.

Its classic three-button placket adds a touch of versatility to your casual style, while the fabric's softness ensures a relaxed yet polished look. Ideal for layering under a jacket or wearing solo, this Henley strikes a perfect balance between casual and refined, making it a great go-to option for everyday style.

Wrangler Authentics Long Sleeve Waffle Henley

The Wrangler Authentics Long Sleeve Waffle Henley is a staple for casual comfort and rugged style. Made from a cotton-polyester blend, this shirt features a waffle-knit texture that adds warmth and breathability, making it an excellent choice for layering or wearing on its own.

The three-button placket enhances versatility, allowing you to adjust for comfort and style. Designed for a relaxed fit, it provides ease of movement, whether you're lounging or on the go.

Available in various colors, this Henley delivers timeless appeal with durable construction, making it a reliable addition to any wardrobe for year-round wear.

 

How to Style a Henley Shirt

Henley shirts offer exceptional versatility, making them a staple in any wardrobe. Their ability to transition seamlessly between casual and dressy settings makes them an easy go-to for various occasions. Whether worn on their own or layered, Henleys provide a stylish and practical option for different outfit combinations.

For a relaxed, everyday look, pair a classic Henley with jeans and one of your best white sneakers. This combination is effortlessly stylish and perfect for casual outings or weekend wear. If you want to elevate the outfit slightly, opt for slim-fit chinos instead of jeans.

The addition of chinos refines the look, creating a smart-casual aesthetic that works well for date outfits or casual office settings. Layering is another great way to incorporate a Henley into your wardrobe. Wearing one under a leather or denim jacket adds depth and texture to an outfit while providing extra warmth during cooler months.

For a rugged, masculine appearance, consider styling a Henley with dark-wash jeans, a flannel shirt, and Chukka boots. This combination exudes an effortless yet put-together vibe, making it perfect for fall and winter wear.

If you're aiming for a dressier look, opt for a fitted Henley in a neutral or darker color like black, navy, or charcoal. Pair it with tailored trousers or dark slacks and complete the suit with loafers or dress boots.

This polished take on the Henley shirt works well for business casual environments. Accessories like a leather belt or an affordable watch can further enhance the refined appearance.

Regardless of the occasion, Henley shirts offer a flexible and stylish foundation for countless outfits, making them an essential piece in any modern wardrobe.

 

Casual Outfit Ideas with a Henley

Classic Casual

A short-sleeve Henley paired with jeans and sneakers is a timeless and easy-to-wear look. This simple yet stylish combination works for daily activities, from running errands to meeting friends.

Choose a Henley in neutral tones like grey, white, or navy for versatility, and pair it with slim or straight-leg jeans for a streamlined silhouette. Opt for comfortable sneakers to complete the look, ensuring both style and practicality.

Layered Look

Elevate your casual outfit by layering a long-sleeve Henley under a denim or leather jacket. This combination adds texture and dimension to your outfit while keeping you warm on cooler days

A darker-toned Henley, such as burgundy or deep maroon, contrasts well with the jacket, creating a balanced, visually appealing look. Pair with chinos or rugged jeans and Chelsea boots for a stylish, edgy outfit that’s perfect for casual weekends or nights out.

Laid-Back Summer Style

For warm weather, a lightweight Henley with shorts and boat shoes is the perfect pairing. The breathable fabric of the Henley allows for comfort on hot days, while the shorts keep the outfit relaxed and casual.

Boat shoes add a touch of sophistication while maintaining a carefree vibe and make for the perfect resort attire. Stick to light colors like beige, pale blue, or white for the Henley, and pair with tailored shorts for a put-together yet easygoing summer look.

 

Business Casual Outfit Ideas with a Henley

Henleys can seamlessly fit into a business casual setting when styled correctly. Opt for a fitted, high-quality Henley in neutral or muted tones such as navy, charcoal, or olive.

These shades can be easily dressed up without sacrificing comfort. Pair the Henley with a well-fitted blazer. Add a pair of dress shoes, such as leather loafers, derbies or oxfords, to enhance the sophisticated vibe while maintaining the casual appeal of the Henley.

For a versatile and modern business casual look, try a navy or charcoal Henley under an unstructured blazer. This combination strikes a balance between laid-back comfort and professional refinement, making it ideal for a day at the office or a business conference.

Avoid overly bold colors or patterns, as they can distract from the clean lines and subtle elegance of the outfit. Keep accessories minimal, like a simple 38mm watch, for a clean finish.

 

Best Colors for Henley Shirts

• Neutral Shades: Colors like white, grey, navy, and black are classic choices for Henley shirts, offering versatility and timeless appeal. These shades are easy to style and can be paired with almost anything in your wardrobe.

• Earth Tones: Olive, burgundy, and brown Henley shirts bring a rugged, grounded feel to your wardrobe. These rich, earthy colors are perfect for adding depth and warmth to your look, making them ideal for fall or casual weekend outings.

• Pastel Hues: Light pastel colors like soft blue, mint green, or light pink are excellent choices for summer. These shades exude a relaxed, breezy vibe and can help keep you cool while looking stylish in warm weather.

The ideal color for a Henley shirt often comes down to personal style and how the color complements your existing wardrobe. If you prefer a minimalist look, stick with neutrals, which can easily mix and match with a variety of outfits.

 

Henley Shirts for Different Body Types

One of the reasons Henley shirts are so popular is their flattering fit for various body types. For those with a lean build, a slim-fit Henley enhances the frame without looking too baggy.

Men with athletic builds benefit from the structured design that highlights broad shoulders and a toned physique. If you have a larger body type, choosing a Henley with a relaxed fit and a looser drape helps ensure comfort without being too tight.

The button placket also allows for adjusting the neckline, which can create a more elongated effect for shorter individuals.

 

FAQs About Henley Shirts

What is the difference between a Henley and a tee shirt?

A Henley is similar to a T-shirt in that they both have short sleeves, but features a buttoned placket at the neckline, typically with two to five buttons, whereas a T-shirt has a simple round or V-neck without any buttons.

Henleys also often have a slightly more structured and rugged look, making them a versatile choice for both casual and slightly dressier outfits.

Who should wear a Henley shirt?

Anyone can wear a Henley shirt since its invention at Henley on Thames, but it particularly suits those looking for a casual yet stylish alternative to a basic tee.

It’s a great option for men who want to add subtle detail to their outfits without going overly formal. The buttoned neckline also makes it flattering for most body types, adding structure to the chest and shoulders.

What is the difference between a polo and a Henley?

When considering what is a Henley shirt, the main difference between a polo and a Henley is the collar.

A polo shirt has a fold-down collar with a buttoned placket, often associated with preppy or semi-formal style, while a Henley has a round, collarless neckline with a buttoned placket, giving it a more relaxed and rugged appearance.

Polos are often made from pique or cotton blends, whereas men's Henley shirts are usually made from soft cotton or waffle-knit fabrics.

Does a Henley shirt have to have buttons?

Yes, a Henley shirt is defined by its buttoned placket, typically featuring two to five buttons.

While some modern designs may mimic the Henley style without functional buttons, a true Henley always includes this signature feature, distinguishing it from a regular T-shirt.