Dressing For A First Date

We’re all victims of a grand fashion conspiracy: grown women are being made to believe they haven’t got a clue as to what to wear! How else can you explain the proliferation and popularity of makeover and style counsel television shows? We’ve gone from our mothers shrieking, ‘You’re not leaving the house in that!’ to unsuspecting women being fashion ‘punk’d by cable style shows. All this unsolicited, yet 24/7 advice has us second-guessing our wardrobes and our ability to get dressed for that all-important event: The First Date. But do you really need a perfect dress to snare the boy next door?

I’m convinced that clothes do not make the woman or cause the man to fall head over heels for a lady in Manolo Blahniks. I’ve yet to hear a man say ‘I fell in love with her when I first saw her in that Calvin Klein summer dress . . . You remember the one, honey, with the buttons down the back.’ More likely he remembers being turned on by seeing you in one of his old button-down shirts.

Still, I have considerable first-date experience and I’ve had my share of panicked pawings through my closets looking for the ‘perfect’ ensemble for that initial evening out. I’ve also spent years observing couples on their initial hookups, and combined with my fashionista past, I have come up with some common sense rules for a first-date dressing success.

1. Don’t wear black. It’s already dark enough in that club, restaurant or movie theater you’ll probably wind up in. Your mission is to stand out, not blend in with your surroundings. Besides, my unofficial poll of single guys found that they find the color totally desperate and boring.

2. Don’t wear your closet. This is not the time to layer your favorite shirt underneath that gorgeous sweater you just couldn’t resist from the mall and cover them with ropes of chains and pearls. With that much eye candy, your guy may have trouble figuring out where to focus. You’re trying to win a personality contest, not ‘Project Runway.’

3. Don’t show up in anything that makes you look like you’ve been wrapped, twisted or tied up in knots. This only leads to wrong-way thinking on his part, such as, ‘How did she get into that get-up . . . and how am I supposed to get her out of it?’ Besides, throwing out hints of one’s personal bondage fantasies constitutes way too much information on the first date.

4. Focus on looking great above the waist. Chances are, most of the evening you’ll be sitting down. Spend your resources presenting a pretty picture that he can see. Give him something to talk about: a blouse in a great color, a well-made top that shows off your shoulders, or jeweled earrings that catch the light. He may not necessarily know fashion, but most people know what they like in colors and shapes: that color on you, the shape of the shirt on your curves.

5. Embrace color. You don’t have to dress in a Technicolor splash, but a little color around your face will bring out your eyes and your smile. The right shade will make you look rosy when you feel ill from the food or something he says. Men love red – from fire engine to cherry tomato to raspberry rich red. Sensuality and sophistication demand that you choose the appropriate shade for your skin tone. Adopt a signature shade. Use the rich hue to get up close and personal.

6. Fit and flatter. Don’t worry about size. Focus on fit. When the dress is on you it should fit you and not your imaginary size. Be real: we all have bags we don’t want to carry and rolls we wish would roll away. The important thing is to master the art of disguise and invest in your assets. When that dress is lying on the floor, I guarantee you he won’t be looking at the size on the tag.

7. Lastly, a first date is not the same as the big reveal. Flaunt your best features, but not all of them at once. A plunging neckline does not need to compete with a thigh high skirt. Less is more. The less you show now, the more you’ll have for later.


My friend Heather keeps Polaroid pictures of herself in her favorite outfits. She readily admits to having more clothes than she can remember, so she has complied a record of her fashion inventory and what looks best on her. When she goes shopping she takes a few photos along for inspiration and moderation. You could take her idea one step further and categorize your favorite looks. Note which is your favorite interview suit, jot down which dress makes you feel like a million bucks and put together a dream collection of first date styles.

Here are some style guides in case you’re not convinced of your own fashion savvy. Also, you can find more haute tips at www.thelastsinglegirlintheworld.com.

Shop like a pro in the world’s fashion capitals with the Where to Wear 2005 guides for different cities: Las Vegas, New York City, Paris, Italy (Florence, Rome, Milan), San Francisco, Los Angeles and London

Television homework: watch a few episodes of What Not to Wear. It’s amusing and you can comfort yourself by saying ‘I wouldn’t wear that!’ Either the British or the American version will give you the courage to attack your closet and rethink your style.

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