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How to Dress on a First Date (Women)

Updated on October 30, 2009

Ladies, first dates can be wonderfully exciting, but that doesn't mean you ought to get too carried away with your attire. Yes, men do enjoy having a good look at you, but you've got to mind how much you show them. Or rather, you ought to mind how much you show them on a first date. I'm not suggesting you dress up like Laura Ingalls, but neither do I think you should be emulating Julia Roberts in Pretty Woman. I don't care how liberal and freethinking you are -- the fact is, men do judge you by these things, whether they admit it or not. And while some of them would surely love to have you show up to dinner in thigh high boots and nothing else, most decent men would actually be put off by such things, unless they were paying for your time (if you get my meaning). Don't get me wrong -- I'm not saying don't dress sexy. I'm just saying don't overdo it.

1. Dress like you respect yourself.

If you've got your girls popping out of your blouse this does not convey self-respect, it actually conveys massive insecurity. There's nothing wrong with showing them off, but if you put too much focus on them it comes across as though that's the best thing you've got to offer. And if it is, you're not going to keep his attention very long. Men like to be teased, not overwhelmed. Show them too much too soon and they'll get bored quickly.

2. Dress comfortably.

Don't get dolled up in something you're going to feel like an idiot in, as that could easily affect your mood. You don't have to wear sweats and trainers to dinner, but you should be wearing something you can feel good in for the entire evening.

3. Dress for the weather.

Don't wear something made of wool in August just because it looks good on you and then hope your date will be taking you somewhere air conditioned. If he surprises you with a picnic in the park you're going to look like a real princess if you start whinging about the heat. Likewise, don't wear a miniskirt during a blizzard just because you think he'll like your legs.

4. Dress for the occasion.

This should be common sense, but it seems that some women go out of their way to prove it isn't. If you're going to a sporting event, a slinky sexy dress and stilettos is not appropriate. If you're going on a hiking trip, chunky platforms are not going to work very well. If you're going to a nice restaurant, sweats and sandals are going to make you look like a redneck.

5. Wear clothes that FIT.

If you're a model with a size 4 waist and stuff yourself into a pair of size 0 britches -- guess what? You're still going to have a muffin top. Wear clothes that fit you and you won't have to worry about this. Show up at a party wearing clothes that belong on someone much smaller than yourself will make you look silly.


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