Secrets To A Perfect Date Outfit

By Catesby Holmes. Posted on Nov 15th 2008.

The perfect date outfit can be hard to find. Tips on how to make your wardrobe dateable.

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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