Best Bet: Wood Wood Regina Skirt

After eight months of wearing jeans, it’s time to swap some skirts into the rotation. Wood Wood’s Regina skirt’s front pleats and high waist create a flattering silhouette without ballooning at the hips. Paired with a silk tank and heels, the style works as well for the office as nights out. And in 100 percent cotton, it won’t crease like linen or silk.

Wood Wood Regina skirt, $134 at Dear Fieldbinder or online.