All right, look, I'm gonna tell you something—though it's not exactly a secret or anything—but you gotta promise me something:
PLEASE. TRY. TO. NOT. LOOK. LIKE. A. HOOKER.
I'm not sure why, but shorts seem to be a difficult thing for some women to grasp. Not everyone's 6-foot-2, leggy and gorgeous, but there's something for everyone, I promise.
Keep the shorts fairly simple: tailored or grungy, patterned or solid, conservative or loudly colored, that's all up to you—but as a general rule of thumb? Swarovski crystals and clothing? Usually not a good combination. Especially when the crystals are Bedazzled onto the seat of the pants. C'mon, guys. This should be pretty obvious, but for some reason, girls flocked to the crystal-adorned Seven-for-All-Mankinds that came out not too long ago like raccoons to shiny objects. Not only are the crystals pretty pricey, but they also cheapen clothing terribly and have the tendency to fall off in the wash.
As for the length? Totally up to your body type. Cute, little bird-like frames or leggy types = the short shorts. Not? Mid-thigh or knee-length are great, too.
This girl has on one of my favorite easy-but-head-turning groupings that has been popular in the hipster (God, there's that word again. I'm sorry. I really, really am) circuit for a few years now. It's simple to pull off and definitely flattering for many body types, and you'll look cute as shit.
Keep this general tutorial in mind: longer, loose, wispy, tunic-like tops (unbelted—or if need be, thinner belts generally do the trick. Those wide-as-hell pleather Wet Seal waist-belts that people have been sporting right under their huge racks are far from attractive, much less are they "waist-defining." Y'all just look top-heavy), shorts and a pair of really great boots (mid- to full-calf length). Make sure the bottom hemline of the shirt you're wearing meets somewhat closely to the bottom of the shorts for a ridiculously cute Brigitte Bardot babydoll thing—or not, like this girl has decided.
Her simple, red, loose-fitting shirt and not obscenely short shorts go great with a pair of unadorned brown-leather boots. A glass of red wine and a couple o' strands of small yellow beads, and she's ready to go. Totally adorable.
Feel free to swap out the boots for some strappy sandals, but that's where the tricky prostitute (or slut—your choice!) comes into play: the more skintight (or worse—belly-baring!) the top, the taller the boots, the higher the heels, the shorter the shorts, the higher your chances are of looking hooker-y.