How to Wear a Henley

Co-authored by wikiHow Staff

Last Updated: June 17, 2021

Henley shirts are a wardrobe staple, easy to wear and sexy. Dress them up or keep them casual, layer for warmth or wear a short-sleeve version in warmer weather. Wear one under a suit coat at work or layer under a sweater for a casual date. Accessorize with shoes, belts, and jewelry to complete your outfit. This go-to piece will quickly become one of your favorites.

Part 1

Part 1 of 3:

Wearing a Henley Casually

1
Try layering your Henley with a button-down shirt in cooler weather. When the weather turns to cooler temperatures, throw on a button-down over your Henley. You'll be stylish and warm. #*Alternatively, you could wear a pair a sleeveless Henley with a sleeveless button-down in warmer weather.
- Patterned shirts go well with Henleys. Choose a color found in your shirt pattern, or go with a neutral like black, white or gray.
2
Wear a jacket or a sweater for a pulled together look. This works equally well under military-style coats, jean jackets, cardigans, and V-neck sweaters.
- The buttons on a Henley will bulge under a crew neck sweater. Choose a cardigan or V-neck instead.
- If you layered your Henley over a tank top or undershirt, you may want to adjust the undershirt to avoid wrinkles or discomfort.
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3
Combine your outfit with jeans for a casual, easy vibe. Henley shirts go perfectly with jeans, distressed or not. Unbutton your Henley to reveal a bit of a tank top or an undershirt. This look works well for both men and women.
- Baggier boyfriend-style jeans will give you a more casual look than a skinny jean or a men's straight jean.
- Faded washes tend to look more casual than uniform dark washes, and your jean wash will impact how dressed up or casual your Henley looks.
4
Wear your Henley with leather or pleather pants for a night out. For a sexy look, do a half-tuck and unbutton two buttons. The look is tough and effortless for a fun night out or a casual date.
- Whisper-thin Henleys will go equally well with leather/vegan pants as a heavier thermal-style Henley.
5
Use a casual skirt for running errands or grabbing brunch. A skirt is as easy to wear like jeans, and a Henley will work with a denim mini skirt or a fuller skirt.
- If you opt for the fuller skirt, make sure to tuck it in to maintain a streamlined look.
- Short or long-sleeved Henley's work with casual skirts.

Part 2

Part 2 of 3:

Dressing Up a Henley

1
Wear dressy jeans for the ultimate versatile outfit. Really, you can wear this outfit almost anywhere and feel great. Dark jeans in a uniform wash look dressier than their distressed and faded counterparts.
- A heel or dress shoe will immediately dress-up the entire outfit, as will a suit coat or a faux fur or leather/vegan jacket.
2
Add a dressy skirt or pants for work or a date. You can layer a Henley sweater over a tank or tee and pair it with a dressy skirt or pants. This elevated look can take you from day to night.
- A thin ribbed Henley with short sleeves is a good choice to wear with a career skirt or dress pant.
- You can wear a Henley under a suit coat. Smooth fabric Henleys will read as dressier than waffle fabrics.
3
Choose a sleek Henley dress for a bodycon look. Choose a body-con Henley dress in a premium fabric that hits just below the knee. Throw on a suit jacket and heels to elevate the look.^{[1]
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- Shorter Henley dresses in looser cuts will look more casual, but still cute, with flip-flops, tennis shoes, or flats.

Part 3

Part 3 of 3:

Accessorizing a Henley

1
Include a necklace for a little polish. Both men and women can accessorize their Henleys with necklaces. Shorter necklaces will show when the shirt is unbuttoned. Longer necklaces can work over or under a Henley. Pendant or simple chain options will go better than large jeweled chokers.
- Wearing a completely unbuttoned Henley with a very long necklace will draw your eye down to where the necklace lays.
- If this isn't the look you are going for, button one more button or wear a shorter necklace.
2
Use footwear to drive home your vibe. Second, to what bottoms you wear, your shoes may very well drive the vibe of your outfit. From a sexy heel to a hiking boot, the sky's the limit here for both men and women.
- Moto boots will toughen up your look. They can be worn with straight jeans, over skinny jeans, or with a mini skirt.
- Tennis shoes help to play it down when you are running errands, but a polished leather high-top might turn you toward a coffee date or casual dinner.
- Men's dress shoes are a great option for suit pants, dressy jeans, or chinos.
3
Slip on a belt to finish things off. Belts are a great way to give outfits a tailored, put-together look. From simple to extravagant, the choice has to do with the vibe you are projecting. A thin leather belt can be worn around the waist of a Henley dress. Thicker embellished belts go great with jeans and boots.
- Women's high-rise jeans and a tucked in Henley will benefit from a belt. Choose one that fits the width of the belt loops
- A half-tucked shirt looks great with a belt. Tuck in a little bit slightly askew to the middle. It should look effortless and reveal part or all of your belt's buckle.
- Avoid wearing an untucked Henley over a belted pant. The belt will bulge under the Henley.