The perfect date outfit can be hard to find. Tips on how to make your wardrobe dateable.
By catesby holmes — Written on Nov 15, 2008
Every morning we get up and put on clothing. So what makes figuring out what to wear on a date—especially a first date—so difficult? When meeting someone we (might) want to kiss later, picking an outfit becomes less about promoting modesty and protecting from the elements and more about the message we want to convey: alluring but not easy, smart but not stuffy, playful but not a lunatic. That's a lot of pressure. But in those frantic pre-date moments when clothing is piling up and the minutes are ticking down, go for the always-alluring, fail-safe staple guaranteed to prevent a stripes-with-plaid-with-polka-dots catastrophe: The Dress.
They say that first impressions are everything. Never is that quite so true as on a date with a new guy, when the pressure's on to convey—in a single glance—confidence, style, and sex appeal. Wardrobe decisions may induce some serious pre-rendezvous panic, but the fact is that the anxiety is warranted: every guy I polled about this topic confirmed that what a girl's outfit can set the tone for the evening.
"I still remember when a date showed up wearing jeans and a plain white T-shirt the first time we went out," says Greg, a 26-year-old law student in New York City. "She looked good, but the lack of effort was disappointing—I consider the time invested in an outfit a possible indicator of how interested she may be in me."
Of course, you don't want to overproduce your look, either. If jeans and a t-shirt indicates a possible lack of interest, a cocktail dress with stilettos can read as desperation. "I like to get a sense of a woman's body from what she's wearing," says Eric, a musician. "But I also get turned off if her clothes are too revealing."
To help YourTango readers strike this difficult balance, we put together this What to Wear on a Date guide. Our goal? To outfit you in attire that says all the right things when you walk through the door, namely: Hi, I'm me. These clothes? Well, they reflect my personality and sense of style. I'm confident about myself, interested in you, and ready to have fun—though exactly what ‘fun' means is still my secret.
Footwear. Let's start with the absolute basics: is your date short or tall, compared to you? For a first date, you'll probably want to maintain the whole "men are big, tall, and strong" stereotype—it's definitely an ego boost for him, and at the very least safe bet for you. So pick heel height accordingly. If the lucky gent is within three inches of your height, opt for a flat, like a ballet slipper or stylish sandal. For taller men, a higher heel is an obvious and sexy choice—just be sure you can walk in your footwear. A face-plant is never sexy.
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The clothes. Unless you're going on a sporty date—say, rock-climbing—I prefer dresses to a skirt-top or jeans-blouse combo. Dresses are flirty, fun and feminine, and can run the gamut from a casual sundress (for coffee) to a fancy frock (for a night on the town). However formal the dress, pick one (just one) feature and play it up: exposed backs are titillating without being overtly sexual, a halter reveals just a suggestion of cleavage. If you want to show-off some leg, choose a hemline that's short enough to intrigue but long enough to cover your bum when you bend over. All in all, your outfit—be it dress or otherwise—should hint at how great you'd look without it on, while leaving plenty to the imagination.
Jewelry. The most important function of your jewelry is to compliment your good features. For example, if you have lovely green eyes, consider earrings that accentuate their color. If you want to attract attention to your beautiful breasts, a long drop necklace will draw the eye down. Just remember that either the necklace or the earrings—and not both—should be the attention-getter. Another idea is to wear jewelry that is meaningful to you, like a family heirloom or an item you picked up while traveling. It will be unique and serve as a conversation starter.
Make-up. Just as your mom always said, good make-up looks like no make-up at all. So opt for a subtle and natural look—it sustains the image of not having overly prepared for the date. First, even your skin tone with spot concealer and tinted moisturizer; then add dimension with a bronzer or blush, highlighting your cheek bones, forehead, nose, and chin; apply mascara and eyeliner; and finally, add a dash of color with some eye shadow and colored lip gloss.
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If all this advice is starting to stress you out, also consider these words from one of the men I polled: "Does how a girl dresses matter? Of course it does—but not nearly much as women would expect. As long as her outfit doesn't portray her as someone she's not—like a librarian or a skank—then it's cool." In other words, ladies: no matter what you slip on, make sure it's you. The hottest thing you can make yourself look like is…yourself.