How to Style a Henley Top Endless Ways

A Henley top comes in many forms:  as a t-shirt with or without sleeves, with or without embellished cuffs; as a sweater; as a tunic; as a peasant blouse; as a plaid shirt; embellished, embroidered, ruffled, printed, metallic, etc.  With it’s many variations and fabrics, it can be dressed up or down and worn any time of the year.  It’s a great layering piece for the fall and winter, or even in the spring and for casual business in the summer.

There are infinite possibilities!  And because of the endless styling options, age doesn’t matter.

Here are some outfit formulas for styling and layering a Henley shirt, followed by 25 ways to combine it in your outfits.

What is a Henley?

The Henley is a collarless pullover with a short, button-up placket.  It originally debuted in 19th century England as the preferred attire for rowing crews participating in the Henley Royal Regatta.  It then caught on as a men’s undershirt, and is still popular among men worldwide.  Later, when women began to wear Henley shirts, the sleeve lengths and fabrics began to vary, prints were incorporated, and details were added such as hoods and ruffles.

Ways to Wear It

Henley shirts can be dressed up or dressed down and can be worn any season, depending on what you wear it with.

Pick a Henley shirt that has a bit of “slouch” to it, meaning one that isn’t tightly fitted to the body but pulls away a bit.  For a hint of sexiness, keep the first two or three buttons open.

Outfit Formula #1

Wear your Henley shirt with a pair of jeans.  To dress this up, add a pair of pumps, whether basic black or a wild animal print.  When leaving a few of the buttons on your shirt undone, you have the option of adding glitter to the neckline with a necklace.  Keep it short so it does not dangle down into cleavage.  You can use a statement necklace or a simple silver or gold necklace.  Polish off this outfit with a classic blazer in beige, tan, navy, black, ivory or white.  Since the Henley shirt is already slouchy and of a masculine background, stay away from the boyfriend blazer.  Instead, choose a more fitted blazer, which will give you a basic chic look.

Outfit Formula #2

Show Some Cami:  A pretty way to wear a Henley is to layer a fitted camisole underneath to streamline your shape and add extra coverage to thin fabrics.  You can choose a shape-wear cami for support.  Or, you can show off a colored cami or lace trim by leaving some or all of the buttons undone.

Bottoms Up:  The comfortable, relaxed look of a Henley is the perfect complement to your favorite jeans.  Twill pants and khakis transition your Henley from lounging to casual workplace.  A skirt paired with a Henley is an effortless feminine look, ideal for a date or a girls’ night out.  Since Henley shirts come in a variety of fabrics and sleeve lengths, they can be combined with seasonal bottoms.  For instance, try a long-sleeve sweater Henley with corduroy pants in the fall and winter, and a short-sleeve cotton Henley with shorts or a lightweight skirt in the spring and summer.

Top It Off:

The Henley shirt is great for battling winter bulk.  They are form fitting and available in thin but warm fabrics such as thermal knits and flannel.  The Henley adds a layer of cozy warmth under shirts, sweaters and jackets.  During warmer months, you can create a polished look with a lighter-weight cardigan, jacket or blazer.

Accessorize:

The buttons on a Henley draw the eye to your chest, neck and face.  Use this to your advantage by framing your face with a necklace, scarf or earrings.  A necklace is most flattering if your Henley is completely or partially unbuttoned.  Since most Henley shirts are casual and understated, add a touch of glam by selecting an eye-catching piece of jewelry or a fabulous bag.  If your Henley is long, cinch it at the waist with a belt — a wide one for a boho-chic look or a narrow one for a preppy look.

Outfit Ideas Using A Henley:

1. Day to Evening:  A gray Henley over a white camisole + gray flannel pants.  For evening, add a metallic belt.
2. A fitted black Henley + printed palazzo pants with a black ground + a black leather jacket.  Add a chunky gold chain necklace + gold bracelets, maybe with a gold watch in between + black heels.  You might like to dress this up a little more by putting your hair up and adding a clutch.
3. A thermal Henley + harem pants + a long cardigan + ankle boots.

   

4. A leopard-print tee with a low-enough neckline to show buttons of a fitted layering Henley + a leather vest + skinny trousers in the same color as the vest.  Add gold bracelets on both wrists.
5. A beige safari-style jacket + a gray thermal Henley half-tucked into blue jeans.  Add a long pendant with charms to come just below the placket + dream-catcher earrings.  Or accessorize as desired.
6. A Henley sweater + khakis or cargo pants.  Add jewelry (hoop earrings, bangles, etc.)
7. A Henley + a maxi skirt.  Layer chain necklaces in neckline.
8. An embroidered Henley over a long floral skirt or a long chiffon skirt.  Add flat nude sandals + a short delicate chain necklace + special hoop earrings + a delicate chain bracelet.  Push sleeves, if any, up to elbows.
9. An embroidered white Henley tucked inside an embellished black crinkle skirt.  Add a tan belt + flat black sandals + layered necklaces + metallic earrings + a black & white cuff + a big ring + a brown suede purse. (Vary any of these colors or textures according to what you have.)
10. A cardigan + a Henley + blue jeans.  Add belt, scarf, earrings, rings.

    

11. An embroidered Henley + a boyfriend cardigan + blue jeans.  Add a scarf looped around loosely with ends in front + metallic bracelets + hoop earrings.  Or, on a cold day add a leather cord necklace with a beanie, convertible mittens, snow boots.
12. A chambray or denim shirt worn open as a jacket over a Henley.  Add bottoms of choice.
13. A Henley + a zip-front hoodie + blue jeans.
14. A plaid flannel shirt worn open as a jacket over a Henley + a long printed scarf + blue jeans.  Add tan ankle boots + bracelets + a big ring.

    

15. A Henley + a short jean skirt.  Add a gold bangle or two + earrings.
16. A Henley + cargo pants.  Add a charm necklace.  If the Henley has long sleeves, push them back to show a leather bracelet.
17. A black Henley front-tucked into blue jeans.  Add a brown belt + a short pendant + delicate earrings + fingerless gloves for warmth.
18. A Henley unbuttoned over a blue or gray or other color tank top + blue jeans.  You might like to add a hoodie and/or a necklace.

    

19. A white embroidered Henley over blue jeans.  Unbutton enough to accommodate a short pendant.
20. A teal, turquoise, aqua, coral or red Henley + blue jeans.  Add a short coral & turquoise necklace.
21. A Henley + blue jeans.  Add a couple of gold necklaces, such as a short coin necklace + a short pendant.

    

22. A jean jacket + gray Henley + gray corduroy pants.
23. A black Henley + gray corduroys.  Add black ankle boots with a heel.
24. A fitted thermal Henley + a draped tank top over it + blue jeans.
25. A Henley + blue jeans + a scarf tied in neckline.

    

If this was helpful to you or you try any of these tips, let us know in the comments below.  What are your favorite ways to wear a Henley?  We’d love to hear your tips!  

Like this post?  You might also like to read:

• “How to Look Great in the Cold?  Layer Up!”
• “101 Ideas for How to Use Scarves in Your Outfits”
• “Here Are 45 Sure-Fire Ways to Rock a Kimono”

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Outfit formulas in this post were adapted from past articles “How to Wear a Henley Shirt,” and “What Do You Wear With a Henley?” by Marissa Meyer.

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Outfit Combinations