Wednesday, November 25, 2009

What to Wear on a First Date

One of the great things about first dates is how easy it is to recycle outfits. If you have one dress reserved for first dates, no one will ever know how often you wear it (even if you find yourself pulling it out of your hamper three nights in a row).

We’re not slaves to fashion, and normally we don’t think it’s worth spending too much time thinking about what to wear. But a first date brings out the neurosis in most of us, and if you spend too much time worrying about your outfit, it can put you in the I’m-trying-too-hard frame of mind that never looks good on anyone.

Having a go-to outfit tucked away in your closet can help alleviate pre-date jitters.

But not everyone has the same ideas about what makes a good outfit, so we enlisted the help of two single DCers who never seem to be at a loss for dates. And we threw in our own opinion, just for good measure.

The 9-to-5 Blonde

When this girl goes out, guys take one look at her and open a tab. But she still gets nervous before dates. She went out with a new guy for the first time the other night, and she shared this story about what she wore:

The morning of my first date I heard on the radio that in order to have a successful first date (meaning, he calls you back) you have to show off 40 percent of your skin. (Apparently both arms are 10 percent and legs are 15 percent each.) That led to an entire day of anxiety trying to figure out how I was going to show off 40 percent of my skin in the middle of November. After mentioning this statistic to a few friends, it didn't take long for us to realize that no one other than a man came up with that statistic. Every woman should feel beautiful on her first date and if you feel beautiful showing off 40 percent of your skin in the middle of November, than do it. I prefer to be warm and comfortable. Basically, I decided what to wear based on what makes me feel beautiful. I chose the color black because it is slimming and classy. This black sweater dress is tight around my waist and really shows off my body without revealing a lot of skin. I wore tights and knee-high black boots to give it a wintery look. I topped the outfit off with a silver necklace to add some color other than black. When he picked me up the first words out of his mouth were, "You look great." The 40 percent skin rule isn't really a rule at all. Wear what makes you feel beautiful and you will come across as a confident and classy young woman that he can't wait to spend another night with.

The Black Card Beauty

When this girl goes shopping, she tells them to put it on her account. But she says most guys can’t tell Fendi from Forever 21, so she only advocates telling them to put it on her account if it actually looks good:

I think a lot of girls will spend $500 on a boxy dress that just isn’t flattering. I always want to look good, and I never want to look like I’m trying too hard. That’s why I almost always wear jeans on a first date: they can go either way. For this outfit, I paired jeans with a really nice top and some bolder accessories. In my opinion, you’re better off splurging on accessories, because you can carry the same bag every day and no one’s going to call you out on it. And if you’re wearing nice jeans and carrying a nice bag, a $20 top can suddenly look like a $200 top. Not that most guys are going to notice stuff like that. And if they do, I don’t necessarily want to be dating them. I also love raiding my mom’s closet—that bag is hers. You’d be surprised by what you can find in your parents’ wardrobes. Finally, I like to wear open-toed shoes on dates. I think they’re very flirty, but in a more subtle way. Anyone can wear something that shows off too much cleavage, but open-toed shoes are suggestive without being skanky. But, on the whole, I don’t think it’s worth worrying about what designer you’re wearing on a first date. If a guy’s judging you on that, do you really want to be dating him?

The Blogger

Like most bloggers, I’m almost always broke, so I don’t advocate actually spending money to put an outfit together. Instead, I always go through my closet and find new ways to wear clothes I already own.

I’m really into the Joan look from Mad Men right now because I think high-waisted skirts are pretty universally flattering. Unfortunately, I don’t own a high-wasited skirt. So I take a regular black skirt and a wide, tight-fitting, elastic belt (preferably one that doesn’t leave a loose end hanging), hike it up so that the skirt’s waist falls at the narrowest part of my midsection and secure it in place with the belt. (Sometimes I need to fold some material in around the zipper if the new placement makes the skirt hang awkwardly.) Make sure that the skirt’s waistline is completely tucked into the belt. If my I’m using a tight skirt, I take a gauzy or loose-fitting white shirt and tuck it into the skirt. And then I use the belt to make it look like skirt and shirt are one piece. If I’m using a loose skirt, I put on a tight-fitting white shirt, and, again, use the belt to make it look like one seamless dress. If you have great boobs, show a little cleavage. If you’re as flat-chested as I am, consider using the tight skirt/loose shirt option (I personally use a skin-tight long tube top from American Apparel that can kinda, sorta pass for a skirt, especially with a guy who knows nothing about clothes), and opt for a shirt with ruffles where there should be cleavage. The clearance section at a store like Marshalls or Filene’s Basement can be a surprisingly good place to find shirts for under $5 that might look hideous on their own, but don’t look so bad when only the top third peeks out from under the skirt. Add a pair of black tights—they make everyone’s legs look better, and some even come with control tops if you’re into that sort of thing. Finally, throw on a pair of heels. Yes, they’re annoying to walk in, but they also have a flattering effect. If you’re looking to blow some cash, maybe invest in a pair of stiletto ankle boots—whenever I go out, my guy friends always point them out to me. And while you’re at it, send me a pair at

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