Easy Outfit Upgrade: Wear Pants Beneath a Skirt or Dress

Easy Outfit Upgrade: Wear Pants Beneath a Skirt or Dress(Sources: Vivien Killilea/Getty Images North America, Ben A. Pruchnie/Getty Images Europe, ImaxTree, Ian Gavan/Getty Images Europe)There will always be those days—or nights—when your wardrobe seems to fail. Hanging in your closet are the same six dresses you wore for the last six days, the scuffed shoes, the less-than-perfect jeans. And yet, life beckons. Plans were laid, dates arranged, cocktails poured.

Throw it all on. Seriously. Take your perfect little party dress and wear it over silken pants and a pair of killer heels. Take a cue from English aristocrat Tallulah Harlech and actress Emma Watson and keep it simple in all black. (Harlech's mother was designer Karl Lagerfeld's muse, so the girl's got chic in her blood.)

Or if your plans are little less chi-chi and a lot more downtown, do as Leandra Medine (aka The Man Repeller) and a New York Fashion Week showgoer did and slip a pair of denim skinnies under a boxy caftan or dress. The only rule here is fit: Do not by any means try to squeeze a pair of pants under an already tight skirt or dress. We're playing with proportions, and the silhouette requires room.

If you love the look but can't stand the idea of actually making the effort, try a pair of trousers literally sewn into a skirt, such as the white version below from Front Row Shop ($79). Or if you're up for the challenge, find a bold dress or skirt (we love this bohemian dress from Chic Wish, $68) and pair it with comfy jeans, such as these from Uniqlo ($39.90).

Easy Outfit Upgrade: Wear Pants Beneath a Skirt or Dress(Source: Chic Wish, Front Row Shop, Uniqlo)