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What to Wear on a Date

January 24th, 2008 No Comments


(picture is from the last “date” I was on, I mean who takes pictures when they go on dates. The guy, who I still adore as a person, became my bf, which is why there is a picture.)

Top by La Rok. What you can’t see: skinny black jeans (brandless. more to come on this), and Marc Jacobs silver shoes with creme python trim and navy leather flower on heel, in other words, INTERESTING shoes

Ok, I realize you don’t want to read an essay on this, so I will be brief.

1. First and foremost, YOU MUST FEEL COMFORTABLE AND FEEL PRETTY in this outfit.  You are putting your best foot forward, and while you might think that is how you look (which as I always say, presentation is very importatnt), your best foot is your confidence, smile, and personalilty. So, while you might get help from friends who make you look a little sexier, apply a little more makeup, just make sure, you are 110% with how you feel.

2.  DO NOT go overboard on sexy.  Remember, you’ve got your money maker, show that off, but don’t show too much.  You’ve already got the date. If you show too much a guy is going to think, well, that’s what everyone gets to see, not special.  Make him want to see more, not think he’s seen it all already. Pick an asset (legs or boobs, NOT tummy! even though we know you work hard on it) and do it well. And stay away from skin tight clothes, it’s just tacky.

3.  Let friends help you.  Whether they tell you or not, they know what your best qualities are, which tops look best on you.  If the pants really do make you look fat, even though they would never say those words. So trust them, they are your friends, they want you to be happy.

4.  Go classic! Most men are confused by trend and style, but they understand simple. Make it sexy with the cut of the top or pants or skirt.  Notice above pic, I’m showing no cleavage, and the top is actually very long, but it’s still sexy because it’s a great color and it flows close to my body.

5. Try to not wear jeans on the first date. Jeans are for everyday, dates are a little special, and guys like to know that you tried, although not too hard (really trivial!).  Anyway, unless you’re going to a concert or a dive bar (which means he is clueless), try a skirt. Dresses are still in.  Doesn’t have to be dressy, just be feminine. In fact, when in doubt, wear a dress.

6. Choose something to stand out.  In my outfit, my top was trendy but simple, and the shoes were rockin! So pick something that’s really amazing, I would suggest an accessory.  This being said, go easy on the fake jewelry.  Less is more, and if it’s fake, make sure it’s tasteful.  Red lipstick on the right color of skin can make a whole outfit pop.

7. Be yourself. Don’t cross your arms. Allow him to be a gentleman. Smile. And don’t drink too much!  Remember, he’s not perfect either, so just have fun.

I hope this helps. If you want me to be more specific, email me. But in the end, it’s about your style, I can’t be in everyone’s closet.