First Date Dos and Don’ts: Surefire Style Tips and Fashion Faux Pas


DinnerIt’s your classic movie montage moment: girl gets ready for date with boy and tries on everything in her closet before finally emerging in an amazing ensemble, her bedroom now carpeted with the contents of her closet. She breezes down the stairs to meet her jaw-dropped suitor, as though she’d thrown on the first thing she saw.

Even in the movies, looking motion-picture perfect isn’t easy. But to extend the metaphor, you want your date to be a romance, not a comedy, drama or horror flick! Here are a few dos and don’ts to make sure you stay on genre:

DO look your best. This is a first impression of sorts, so while you don’t need to reenact the above-mentioned montage, take the time to style your hair, check your teeth for lipstick stains and your dress for wrinkles, and break out a signature piece that shows some personality—a flattering wrap dress, chic cropped jacket or haute pair of leather knee-high boots will do the trick.

DON’T overdo it. Yes, you may want to step it up a notch in the hair, makeup and ensemble departments, but don’t reinvent—this is not the time to try that gelled-up faux-hawk or layer on the multi-colored eye makeup (unless your look is already modern punk). You’ll look like you tried too hard, and your date might get a little scared.

DO plan your look. This will pay off huge. First, you won’t have to tear apart your dresser and undo hours of housekeeping. A frantic, last-minute dash to get date ready will leave you frantic and frazzled—not the ideal state of mind for the already anxiety-inducing event of a first date. You’ll be able to answer the door calm, confident and not covered in sweat. Try on your outfit a day in advance and walk around in it, especially if it’s new, so you’ve tested to avoid any wardrobe malfunctions.

DON’T ask your date what he’s going to wear. Unless you’re going to a costume party or a wedding, this may read as an early sign of co-dependence, or he’ll think you’re a control freak. He’s not your girlfriend…but you may one day become his. Feel free to run a few looks by a gal pal, but leave him out of it, at least for now. If you’re not sure what the dress code is for a particular event, make a general inquiry in the vein of “Is this a formal affair or more casual?” That way you can avoid over or under-dressing without his thinking you don’t know how to dress yourself.

DO dress with him in mind. Use what you already know to make strategic choices. For example: if your date is shorter in height, maybe opt for flats over four-inch stilettos. There’s nothing wrong with a woman being taller than her man, but until you get to know him better, it’s best to be sensitive and not tower over him in case it’s something he’s self-conscious about. If he seems reserved, choose an outfit in the slightly more conservative range. This can be done fashionably without compromising your personal style—layering is a huge trend this season, so instead of that plunging halter dress, pick a jersey dress, layer with a blazer or slouchy sweater, and wrap an over-sized scarf loosely around the neck.

DON’T try to be what you think he wants you to be. Attempting to get a read on exactly what your date is attracted to is a great way to sabotage your chances at easing into a relationship when the real you inevitably emerges. If your style is more feminine but you think he’s into a rock-and-roll girl, don’t show up in head-to-toe Joan Jett leather or, worse, a concert tee featuring his favorite band. You won’t be able to back it up in conversation, he’ll see right through it, and when he walks you to your car and sees your daisy-shaped air-freshener and “Powerpuff Girls” bumper sticker, he’ll either think you’re a car thief or have multiple personalities. Being yourself is the best thing you can do on a first date, even though it’s easier said than done. So if a Nanette Lepore baby doll dress is your style, that’s exactly what you should wear.