How to Dress for Any Occasion

The Occasion: A Good First Impression (a First Date, Meeting the In-Laws, School Functions)

Old etiquette: A conservative twinset and a skirt to show how ladylike you are.

New etiquette: Dress true to your personality―but this isn’t the time to take risks.

What to wear: First and foremost, you should feel like you. "Select an outfit that makes you feel great about yourself," says fashion stylist Joseph Williamson. “If there’s a particular color you look really good in or a pair of pants you’ve gotten a lot of compliments on, start with that.” The cautionary note: As the old saying goes, you never get a second chance to make a first impression, so avoid potential eyebrow-raisers. “Don’t wear anything too tight or short, and don’t try too many trends at once,” says fashion consultant Lauren A. Rothman. “For a first date, pick an outfit that’s colorful and feminine and leaves something to the imagination, like a wrap dress.”
 
An easy but proper ensemble for a school event would be a sheath with a cashmere wrap or trousers and a jacket. When meeting the in-laws, look to your partner for cues about how formal (or not) his family is. (Why deny yourself a cheat sheet?) “Definitely find out their expectations and how they like to dress,” says etiquette authority Lizzie Post. “My boyfriend’s parents were perfectly happy to meet me in jeans and a tee, but others might be more traditional.”