Dress-up different

Personal style, just like the artistic masterpieces of the ever-evolving avant garde, should never be predictable-especially not if you're off for a night on the town. Nothing is certain except death and taxes, so why be a slave to the homogenized “going out” look that dictates evening attire? Swim against the sweaty stream of people at Shooters with recess's tips-all the cool people are doing it, anyway.

Vintage. Not to senselessly repeat the mantra of bohemian wannabes, but there is no better way to assert your fashion independence than through a mélange of second-hand items. Think about it: said items are uniquely yours, and because they are often marketed at costs comparable to those of discount vendors, are entirely affordable. Note: Keep accessories current and young looking, especially at night. The goal is to channel '60s sex kitten Doris Day—not to end up looking like a kitten-breeder in her sixties named Doris.

Unorthodox belts. Simple but true. The gold belt craze is still going strong, but we're aiming to buck the trend here. Girls, try thick leather belts over blazers with a low-cut top underneath, or wear a skinny belt right over your ribcage to cinch a blousy silk top. Men, look past brown leather. A guy friend of mine recently wore a pink '80s Cadillac seatbelt buckled around his khakis to a hot club. Coincidence that he waltzed in despite violating the no-'flops rule? I think not.

Crowning jewels. Assume for a moment that your armoire is chock-full of ho-hum going-out classics. Dark denim-check. Black slinky top-check. Every-girl-has-them gold heels-check. Huge chunky coral necklace, vintage rhinestone button earrings, piles of Mardi Gras beads or enormous cocktail rings? For once, leave your room without the requisite chandelier earrings. Try to bend the rules before you're bent over a walker, because truly adventurous fashion remains reserved for the young.

Proportion. It is a blessing to every possessor of two X chromosomes that full, fluffy, A-line skirts are en vogue. Yet our fear of the flattering garment—“I look like a Cupcake Doll!”—may trump all others as the world's most irrational. Certainly more comfortable than those thigh-skimming spandex ruffles, they can still look alluring with a dainty, revealing top or skyscraping heels. Try also a huge men's Oxford shirt belted stiffly around the waist, worn over a super-short denim mini. Either way, draped folds of fabric evoke a luxe sensuality not found in painted-on clothing. It turns out “skin-tight” and “sexy” aren’t synonymous after all.