I'm not an expert in dating, but I've watched tons of chick flicks. When dressing up for a date, there are just a couple of guidelines that you should follow and you're good to go. To give you an idea of how it should be I collected 5 outfits from fashion bloggers.
DOWN TO EARTH
Guys are easy, period. They don't care about all the glitz and glamour of your outfit, as long as you look good. Nothing says laid back better than a sweater. Choose a cute, bright color so it won't look too casual. Match it with a blouse, just like DulceCandy, for a more sophisticated look.
SEXY BUT GIRLYFitted mini skirt are very popular nowadays. Andy Torres from Style Scrapbook, chose to pair this white one with a loose shirt. The shirt balance the skirt, so it looks sexy but still classy and girly. Let him work his imagination. Add a sequin clutch to give a bit more spice to the outfit.
Dresses are a no-brainer. Just one piece of clothing, and you have half of your outfit together. Besides it's very easy to accessorize. Try a beautiful simple dress like blogger Camille, for a modern and confident look. Nothing is more sexier than a girl with confident.
THE GIRL NEXT DOOR
Studies shows that men likes to feel like their the dominant sex (even when we all know their not). Show him your girly side then. Choose a wide skirt like Annabelle from Viva Luxury, and pair it with a cute blouse.
JUST BE YOURSELF
Just like girls like bad boys, boys like messy girls. Seems like the messier, the better (read: clumsy not trashy). You know, the girl who's not afraid to say something crazy, and the girl who feels comfortable wearing a scarf and a loose shirt on a first date. Just like Annette from The Versastyle.