How To Wear Dressy Shorts

There seems to be a prevailing notion that shorts–even dressy ones–can just be thrown on and everything will be alright. I mean, they’re shorts, they’re easy, right? Wrong, bitches. Dressy shorts, when handled incorrectly, will leave you looking effed up. Lest you, lovely readers, should leave the house in black silk shorts, a tee and Chucks, we’ll show you how to get it right.

Black Silk, Cuffed

These black silk, straight legged, cuffed beauties are the holy grail of classy fancy shorts. Due to their medium length, you’re in limited danger of cooch flashing, the cut is classic and the fabric is thick enough not to sag by the end of the night. Nice. [$143, Johnson Shorts, CoutureCandy]

  • If your night’s dressy but not full-on fancy, a standard racer back tank will do. If you want to get a little more stylish, go with something like the mustard yellow top shown. This one’s particularly nice if you’ve got thin arms, a small chest, and a bit of a pooch. If you’re bigger in the arms or chest though, skip it as you’ll look kind of pregnant. [$109, Milne, Pixie Market]
  • A crisp, classic white blouse works for literally anyone who can fit into it. We like this one because the sleeves are 3/4 length, keeping it light and summery. For a night out, switch the bright necklaces for something darker and more dramatic. [$58, J.Crew]

Biker Shorts, Alexander Wang Style

I’m just going to say it right now: if your legs aren’t really thin and proportional, these are not the shorts for you. (Seriously, you’ll be way more comfortable and figure flattered in the shorts above or below. As my mom’s so fond of saying, “you can hate me for this now, but you’ll thank me later.”) If you are one of the blessed, however, squeeze into these bad boys and have your way with them. [$99, Leyendecker, Shopbop]

  • If you wear a tight top alone with these, you will look like an over the top gym-goer. Instead, try something a tad looser, though not shapeless. This beige top is perfect for the job. [$28, Bebe]
  • For those of you who are in badass shape and determined to show it off as much as possible, fine, go with the tight tank. But please, for the love of god, throw a cropped jacket on over that thing. This jacket works double time in that it would also look sweet with the beige top. [$98, Express]

Sack Waist Pleated Shorts

If you’re looking to emphasize that tiny waist and hide a little hip or tummy, these are the dressy shorts for you. We like that they’re khaki instead of black but still totally dress-up-able. [$90, Twenty8Twelve, Shopbop]

  • For a dressed-down look, a simple black tank will do. Stick with a skinnier strap like this one though or you’ll look blocky. [$34, C&C]
  • The more daring amongst you will go with a rather cool print like this multicolor one. It will look awesome tucked in, promise. [$98, Anthropologie]