11 Ways to Spruce Up a Simple Button-Down Shirt

Get creative.

woman in a button up shirt


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, but it's also anything but boring when you know how to style it and what to pair with it.

To make my case, I've found 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


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. 

Classic-fit boy shirt in cotton poplin
J. Crew Classic-Fit Boy Shirt in Cotton Poplin $70

Available in sizes 00 to 24.

Satin Slip Midi Skirt
Vince Satin Slip Midi Skirt $265

Available in sizes S to XL.

sam edelman
Sam Edelman Addilyn Pointed Toe Mule $120 $48

Available in sizes 5 to 11.

Go Oversize and Accessorize

How to Wear Oversized Button-down Shirt


For a high-fashion feel, opt for a loose, slouchy style. 

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.

slim stretch perfect shirt in stripe
J.Crew Slim Stretch Perfect Shirt in Stripe $70

Available in sizes 00 to 14.

Rigid Stove Pipe straight-leg jeans
Re/Done Rigid Stove Pipe Straight-Leg Jeans $250

Available in sizes 24 to 31. 

Bette Bootie
SCHUTZ Bette Bootie $148 $88

Available in sizes 4 to 12.

Layer It Under a Summer Dress

How to Style Silk Blouse


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 it office-appropriate and cool weather-friendly with a button-down underneath. 

red top
Kobi Halperin Maxima V-Neck Long-Sleeve Silk Blouse $398

Available in sizes XS to L.

Satin and crepe midi dress
Reverie Midi Dress $58

Available in sizes XS to XL.

Orlie Block Heel Mule
Sam Edelman Orlie Block Heel Mule $120 $24

Available in sizes 6.5 to 10.

Let It Hang Off Your Shoulders

How to Wear a Button-up Shirt Off the Shoulder


Another easy way to make a button-down feel fun in the evening is by undoing a few of the top buttons and sliding it off your shoulders. Do a half-tuck into your favorite pair of jeans and call it a night. 

Cotton-poplin shirt
Thom Browne Cotton-Poplin Shirt $550 $220

Available in sizes IT36 to IT48.

Farleigh high waisted slim mom jeans in black acid wash
ASOS Farleigh High Waisted Slim Mom Jeans in Black Acid Wash $56 $45

Available in sizes 24 to 36. 

Medium Le Pliage Cuir Leather Top Handle Tote
Longchamp Medium Le Pliage Cuir Leather Top Handle Tote $640

Pair It With a Pantsuit

Ways to Wear a Button-down Shirt


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. 

button down
Ralph Lauren Collection Capri Striped Cotton Blouse $590

Available in sizes 00 to 16. 

Check suit blazer
Mango Check Suit Blazer $120 $70

Available in sizes 2 to 10. 

Straight cotton trousers
Mango Straight Cotton Trousers $60 $35

Available in sizes 2 to 10. 

Give It a High-Fashion Upgrade

How to Wear Oversized Men's Shirt


If you've been wearing out your favorite classic oxford, 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. 

Bibione striped cotton-poplin shirt
Stefano Ricci Bibione Striped Cotton-Poplin Shirt $849 $389

Available in sizes XS to M.

High-Rise Wide-Leg Patch Pocket Jean
Milly Natalie Tie Waist Wide Leg Pant $375 $278

Available in sizes 4, 6, and 8.

Play With Shape to Give It an Edge

Wearing a Button-down Shirt Unbuttoned


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. 

white shirt
Everlane The Japanese Oxford Square Shirt $68

Available in sizes 2 to 14.

patterned jeans
Isabel Marant Cliffy Embroidered Jean $375 $65

Available in sizes 25 and 26. 

Suede Mule With Bejeweled Buckle
Zara Suede Mule With Bejeweled Buckle $55 $52

Available in sizes 5 to 10.

Leave It Open and Belt It

How to Wear a Button-down Shirt Open


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. 

Drapey Oversized Boyshirt in Pure White
Madewell Drapey Oversized Boyshirt in Pure White $72

Available in sizes XXS to 3X.

Modern Femme Denim Mini
Free People Modern Femme Denim Mini $50

Available in sizes 0 to 12.

Caraa Sling Bag
Free People Caraa Sling Bag $125

Mix It With Fun Prints

How to Wear Oxford Shirt


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. Polka-dots? Yes. Animal print? Absolutely. Plaid? Of course. A wrap skirt is a good way to give the outfit more movement, too.

Oversized striped cotton-blend shirt
Balenciaga Oversize Striped Cotton-Blend Shirt $895

Available in sizes 34FR to 44FR.

Andee Rust Brown Polka Dot Midi Skirt
J.O.A. Andee Rust Brown Polka Dot Midi Skirt $91

Available in sizes XS to L.

Demi-fine 14k gold-plated double-orb earrings
J.Crew Demi-Fine 14k Gold-Plated Double-Orb Earrings $55

Keep Things Classic and Clean

Oxford Shirt With Jeans


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. 

white shirt
Banana Republic Riley Tailored-Fit Shirt $70 $41

Available in sizes XXS to XXL.

BDG High-Waisted Mom Jean
BDG High-Waisted Mom Jean $59

Available in sizes 24 to 34.

Layered Coin Necklace
J. Crew Layered Coin Necklace $40

Tuck Into a High-Waist

How to Wear a Collared Shirt


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. 

Camp-Collar Blouse
Banana Republic Camp-Collar Blouse $75 $64

Available in sizes XS, XL, and XXL

Canopy High Waisted Short
Revolve Canopy High Waisted Short $50 $22

Available in sizes XS to L.

Small Gaia's Ark Bag
Cult Gaia Small Gaia's Ark Bag $168

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