How to Style Our Oversized Button-Up: The Boyfriend Portofino Shirt

Add jeans and sneakers.

An oversized button-up will feel immediately more low-key cool paired with your favorite broken-in denim and sneakers. Tuck an oversized shirt into high-waisted, cropped jeans, then add a chunkier platform sneaker, or let it hang loose over skinny jeans and flat white sneakers. 

Work dress pants and a jacket.

An oversized button-up takes on a polished and professional aspect worn with your favorite dress pants—think flat-front Editor Pants—and a blazer or denim jacket. You’ll want to make sure the shirt is tucked and the jacket is tight and fitted, otherwise the overall look can read bulky and untailored. For a preppy and somewhat retro touch, you could also consider buttoning your shirt all the way up to the chin.

Tie it at the waist.

Rather than tucking away the shirttails of an oversized button-up, consider tying them in a snug little knot that sits just below your navel. (Leave the bottom few buttons on the placket unfastened so you have more fabric to work with.) The jaunty look works well with any high-waisted pant (trousers, jeans, denim shorts) and is especially cute with midi skirts. 

Layer over a dress.

While its roots are in workwear, an oversized button-up doesn’t just need to work as an underlayer. Worn over a summery tank dress—tied at the waist, sleeves pushed up—it can work just like a jacket or blazer, extending the wearability of sleeveless pieces. 

Try it tunic-style.

Streamlined leggings or Ponte pants in a dark, solid tone (black, navy) can serve as a cool base to an untucked button-down. You’ll want to cuff your sleeves to give the look shape and finish with flats or sneakers. 

Finesse the French tuck.

A French tuck, or a half tuck, is a smart way to give an oversized button-up a purposeful finish, while still letting it fall loose and flowy. A French tuck is especially cute with wide leg or bootcut jeans; it can also work with tighter, sleeker pants, too.

Pair it with a pencil skirt.

There’s something pleasingly unexpected in the proportions of a narrow pencil skirt silhouette and the billowy look of a tucked-in oversized button-up. Worn with a classic blazer, a pencil skirt feels charmingly vintage. But add an oversized button-up instead, and the in-office outfit is immediately modernized.

Go short.

An oversized button-up is big and blousy by design. That’s the whole point. Which is why it looks particularly cool worn with the shortest shorts in your closet. A dressier short—think jacquard or tweed—could work, but denim cut-offs look cute, too. Just be sure to tuck the shirt smoothly into the waist and cuff your sleeves; otherwise, the shirt can overwhelm the shorts. Of course, when you’re wearing short shorts, flats (either sandals or sneakers) will look more at-home than high heels. 

Tone on tone.

What color is your oversized button-up? Use that hue as a starting point for a sleek tone-on-tone look. White button-ups look crisp and unfettered paired with white jeans or trousers. Black oversized button-ups can feel city-cool with black pants and shoes. 

It's a tank top topper.

In the same way an oversized button-up can work as an overlayer for lightweight dresses, it can take the chill off cold shoulders in the summer months—or add protection from the heat. If you’re wearing tank tops or sleeveless shells to work, an unbuttoned shirt can add an easy extra layer in chilly AC or blazing sun.