Sometimes there is nothing more satisfying than throwing on an oversized button-down shirt and a pair of jeans on a crisp fall day. No matter how preppy or how minimal, the button-down is a timeless wardrobe staple favored by style icons like Carolyn Bessette-Kennedy and Jane Birkin. With the advent of Instagram-friendly fashion, we may have lost sight of the magic of this classic look, favoring eye-catching corsets and bra tops in place of its looser, more masculine silhouette.
According to the coolest street-style stars, however, shirting is set to be this season’s greatest styling tool—it might never have totally gone away, but it certainly had its moment in the sun again during New York Fashion Week. There were plenty of striped button-downs layered over colorful dresses and worn with long, billowy skirts, while some chose to cinch their shirts at the waist with one-shoulder wrap tops. Of course there were nods to the traditional American prep look too, namely with boxy-cut shirts worn with a sweater over the shoulders and a pair of perfectly fitting jeans.
This season it’s time to recommit to the button-down shirt and use it to express your personal style. Below, here are 18 shirting options to get you started.