11 Ways to Wear a Button-Down That Prove You Can Basically Live In It

Updated 05/05/19

If I could only wear one top for the rest of my life, the choice would be easy (and not because I don't appreciate variation): my dad's hand-me-down oxford shirt. It works as a beach cover-up, office blouse, going-out top, and even a makeshift Halloween costume. Not only is the humble button-down the most multipurpose piece in my closet, it's also anything but boring when you know how to style it and what to pair it with.

To make my case, I rounded up 11 different examples of fashionable ways to wear a button-down shirt that appeal to a variety of occasions, moods, and styles. Ready to get some mileage out of this unsung wardrobe hero? Read on to learn all the stylish ways to wear a button-down to work, dinner, dates, and everywhere in between. Getting dressed is about to get so much easier.

Tie It Into a Crop Top

How to Tie a Button-up Shirt Into a Crop Top
@sylviemus_

Tucked in and buttoned up, this outfit is ready for the boardroom; unbuttoned and tied up, it's ready for a night out. If you need an outfit that will transition easily from day to night, this is it. 

J.Crew Relaxed Chambray Boy Shirt $98
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Available in sizes XXS to 3X. 

Vince Raw-Edge Silk Midi Skirt $285
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Available in sizes XS to L. 

Lanora Pointy Toe Mule
Calvin Klein Lanora Pointy Toe Mule $110 $76
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Go Oversize and Accessorize

How to Wear Oversized Button-down Shirt
@emilisindlev

For a high-fashion feel, opt for a loose, slouchy style like the shirt above. 

If you want to make your classic shirt more exciting, focus your efforts on accessorizing. Think funky sunglasses, statement shoes, and a handbag that adds a pop of color.

Oversized Striped Cotton Shirt
M.i.h Jeans Oversized Striped Cotton Shirt $215 $108
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Available in sizes XS to M.

High Rise Ankle Crop Skinny Jeans
Re/Done High Rise Ankle Crop Skinny Jeans $195
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Available in sizes 24 to 30. 

Slash Heel leather ankle boots
Balenciaga Slash Heel Leather Ankle Boots $950
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Layer It Under a Summer Dress

How to Style Silk Blouse
@honeynsilk

As the seasons begin to change, we tend to forget just how easy it is to repurpose our summer wardrobes by layering them with other items. So don't put your slip dress away just yet. Make them office-appropriate and cool weather–friendly with a button-down underneath. 

Pixie Market Silky Biege Shirt $94
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Available in sizes XS to M.

Cross-back silk-satin slip dress
Nili Lotan Midi Cami Dress $545
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Available in sizes XS to L. 

Loeffler Randall Celeste Mid-Heel Knot Slide $350
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Let It Hang Off Your Shoulders

How to Wear a Button-up Shirt Off the Shoulder
@beigerenegade

Another easy way to make a button-down feel fun in the evening is by undoing the top buttons and sliding it off your shoulders. Do a half-tuck into your favorite pair of jeans and call it a night. And there's also the added bonus of forgoing a bra when styled this way. 

Tenia Stretch Cotton-blend Poplin Shirt
Theory Tenia Stretch Cotton-blend Poplin Shirt $245
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Available in sizes XS to XL.

Addie Distressed Boyfriend Jeans
3x1 Addie Distressed Boyfriend Jeans $325
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Available in sizes 24 to 31. 

Topshop Heidi Slouchy Hobo Bag $55
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Pair It With a Pantsuit

Ways to Wear a Button-down Shirt
@nnennaechem

A pantsuit is the oxford shirt's natural habitat. Paired with a plaid matching set, it will feel more modern and stylish but just as crisp, making it ideal for conservative and creative offices alike. 

J.Crew Slim Stretch Perfect Shirt $70
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Available in sizes 00 to 16. 

Topshop Boucle Cropped Jacket $110
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Available in sizes 2 to 14. 

Topshop Boucle Skirt $68
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Available in sizes 2 to 12. 

Give It a High-Fashion Upgrade

How to Wear Oversized Men's Shirt
@_hollyt

If you've been wearing out your favorite classic oxford and feel ready to throw in another to the mix, consider investing in a high-fashion alternative. Look for one that features some of the classic features with an interesting twist, like color-blocking or exaggerated sleeves. Pair it with some simple wide-leg slacks, block heels, and a top-handle bag and never look back. 

Mini striped cotton shirt
Matthew Adams Dolan Oversized Cotton Oxford Shirt $670
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Available in sizes XXS to M.

Jalisa Cady Wide-leg Pants
Alice + Olivia Jalisa Cady Wide-leg Pants $320
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Available in sizes 0 to 12. 

Frances Oval-frame Acetate Sunglasses
Roberi & Fraud Frances Oval-Frame Acetate Sunglasses $250
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Play With Shape to Give It an Edge

Wearing a Button-down Shirt Unbuttoned
@desertmannequin

We love how this outfit takes all the classic pieces and gives them a quirky, bold edge. The pants feature a classic fit, but the floral embroidery makes them fresh and playful; the mules step things up a notch with a bold fuchsia hue; and the unbuttoned styling gives the oxford shirt an edgier silhouette. 

Mango Concealed Button Shirt $40
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Available in sizes 4 and 6.

Miaou Tommy Pant $175
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Available in sizes 26 and 29 to 32. 

Pink Chloe 85 Fabric Buckle Strap Mules
Attico Pink Chloe 85 Fabric Buckle Strap Mules $720 $369
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Leave It Open and Belt It

How to Wear a Button-down Shirt Open
@sylviemus_

If you thrifted an oversize oxford shirt and it falls within that awkward length between a shirt and dress, consider layering it with a denim skirt of the same wash. Embrace the slouchy fit while giving it a little more shape with a fanny-pack or a simple belt. 

Tencel Lyocell Shirt
Eileen Fisher Tencel Lyocell Shirt $198
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Available in sizes XXS to XL. 

Siren Skirt Natural
Nobody Denim Siren Skirt Natural $149
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Available in sizes 24 to 31. 

Deco Bag in Black
Vere Verto Deco Bag in Black $340
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Mix It With Fun Prints

How to Wear Oxford Shirt
@wethepeoplestyle

A pinstripe button-down is one of the easiest things to experiment with when it comes to print-mixing. This is because the pattern is so classic and simple that it adds just enough contrast without clashing or feeling too wild. Pola-dots? Yes. Animal print? Absolutely. Plaid? Of course. A wrap skirt is a good way to give the outfit more movement, too.

Mango Striped Shirt $15
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Available in sizes 2 to 8. 

Maisee polka dot-print cotton wrap skirt
Lee Mathews Maisee Polka Dot-print Cotton Wrap Skirt $321
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Available in sizes 0, 2, and 3. 

Ceci Drop Earrings
Rachel Comey Ceci Drop Earrings $110
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Keep Things Classic and Clean

Oxford Shirt With Jeans
@ada_oguntodu

Tailored, simple, and clean, a button-down and blue jean combo is the perfect for canvas for just about any occasion. Add some personality with layered necklaces, bangles, and rings. 

H&M Cotton Shirt $18
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Available in sizes 0 to 16. 

MOTO Bleach Lucas Boyfriend Jeans
Topshop MOTO Bleach Lucas Boyfriend Jeans $80
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Available in sizes 24 to 34. 

Topshop Multi Charm Lariat Necklace $28
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Tuck Into a High-Waist

How to Wear a Collared Shirt
@_hollyt

For a tailored and put-together look, simply opt for high-waisted bottoms and then tuck your button-down all the way in. Though still loose and comfortable, it looks more form-fitting and allows you to show off the stylish details of your high-waisted bottoms rather than covering them up with your top. 

Ines Shirt
ALSO Ines Shirt $280
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Available in sizes XS to M.

Waoi Belted Pleated Canvas Shorts
By Malene Birger Waoi Belted Pleated Canvas Shorts $295
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Available in sizes 40 and 44. 

Leather Circle Crossbody Bag
Mansur Gavriel Leather Circle Crossbody Bag $795
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