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Home Fashion: Trending How To Style a Button Up Shirt

How To Style A Button Up Shirt

A button up shirt is the timeless staple that you can dress up, down, twist, tuck and layer a hundred different ways. If you’ve ever wondered how to style a button up shirt, the answer is simple: it works with everything.

From oversized silhouettes to tailored fits, button up outfits can carry you through summer to winter and everywhere in between.

Think button up shirt with jeans for an effortless cool girl uniform, button up with a sweater over for classic layering, or even a button up shirt with a cardigan or vest when you want extra comfort.

However you wear it, this versatile essential is the piece you’ll reach for on repeat.

Here’s how to make the most of it:

  • Experiment with different ties and tucks and you’ll easily get 3 looks out of 1 shirt
  • Style with denim for an everyday cool girl uniform
  • Layer under sweaters or jackets for extra depth
  • Wear as an overshirt for that casual undone energy
  • Play with short sleeve button ups for a chic and comfortable silhouette

Different Ways To Tie & Tuck A Button Up Shirt

Half tuck with an oversized shirt: Wear a cropped bralette underneath, only button the middle, then tuck one side of the shirt up under your bra. Loosen until it sits just right for that off-duty model look. Obsessed!

Smooth tuck: Button your shirt all the way through and tuck it neatly into mid or high-rise pants. Smooth the ends flat under your waistband, add a sleek belt, and cinch it in for a super flattering shape.

Corset layer: Layer a strapless corset over your button up and pair with capris or baggy tailored pants. This is a super chic look for any season.

Cinch from the back: Gather excess fabric at the back of your oversized shirt, secure with a brooch on the outside or a hairband on the inside, and instantly create shape without losing the oversized vibe.

Asymmetrical wrap: Wrap one side of your shirt across and secure at the side seam with a button, safety pin, or brooch. It creates an asymmetric cut that looks like a whole new top.

woman wearing asymmetrical wrap button up shirt

Nitsa Long Sleeve Shirt Blue

woman wearing half tuck oversized button up shirt

Peni Linen Button Down Top Chocolate

woman wearing corset layer button up shirt

Darvell Corset Shirt Blue

SHOP BUTTON UP SHIRTS >

Button Up Shirt with Jeans

A button up shirt and jeans is the definition of an elevated, effortless look. It’s the outfit you throw on without thinking and still get compliments on.

Whether you’re heading to brunch, class, or just running errands, this combo never fails and can be styled a million different ways to suit the destination and occasion.

How we’re styling it:

  • Try an oversized shirt with only the middle couple of buttons done up.
  • Style it over a white tank, lace bralette, or ribbed crop underneath.
  • Pair with straight-leg or baggy jeans.
  • Accessorise with a chunky belt, black sunnies, and bold rings.
  • Finish the look with loafers, ballet flats, or pointed boots.

Button Up Shirt Under a Sweater

This styling hack is peak cool girl layering. A button up shirt instantly adds an elevated feel to any chunky knit, and the contrast of a structured collar with soft knitwear makes it feel chic. The trick is to play with proportions. Oversized shirts peeking out from under boxy sweaters always look intentional.

How we’re styling it:

  • Go oversized so the cuffs and shirt hem peek out under your sweater.
  • Pair with a boxy, slightly oversized crewneck for a flattering silhouette.
  • You can also layer under a fitted cardigan for a preppy aesthetic.

Button Up Shirt Under a Jacket

If you want an easy layering formula that works year-round, a button up under your jacket is it. From oversized shirts under long coats to fitted shirts under cropped jackets, this quick combo is the cheat code to elevated everyday looks.

Our Global Style Director, Char, says, “Oversized shirts look amazing under longline coats. Pop the collar over the jacket and let the cuffs peek through as well. It’s such an easy way to layer during the colder seasons!”

How we’re styling it:

  • Layer an undone shirt over a tank before adding your jacket to complete the look
  • Fitted button ups pair perfectly with cropped jackets like bombers to keep the silhouette chic

Button Up Shirt as an Overshirt

Think of the button up as your easiest throw-on-and-go piece.

When styled as an overshirt, you can add a sleek, elevated feel to your beach day and coffee run looks. It’s lightweight enough to layer, but still adds structure to your outfit. If you’ve just got roped into some last minute plans, reach for your button up shirt!

How we’re styling it:

  • Wear open over your bikini with sunnies for beach and pool days.
  • Go for white jeans and a tube top. Keep it neutral with a cream shirt, brown belt, and slides.
  • Keep it unbuttoned and oversized for that relaxed, undone look.

How To Style Short Sleeve Button Up Shirts

Short sleeve button ups are having a major moment. They’re comfortable, versatile, and super flattering.

Whether you’re going for a sporty, preppy, or party girl look, they’re the kind of essential you can keep at the front of your wardrobe season after season.

How we’re styling it:

  • Pair with micro shorts and tall boots for a statement summer fit.
  • Try with a skort, loafers, and socks for preppy vibes.
  • Go sleek with capris and a fitted short sleeve button up, with ballet flats.

A button up shirt is one of those rare pieces that can do it all. From business to party, classic to cool. Whether you’re layering it, cinching it, or throwing it on as an overshirt, it’s the ultimate wardrobe MVP.

Ready to try it for yourself? Shop our full collection of button up shirts and find more button up outfits on our Instagram and TikTok @princesspolly.

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