A woman makes the dress much more than a dress makes the woman, so pick your girl carefully, the dresses will come after. I figure that a good black dress cannot be beat. But not for the reasons you might think. Not because it flatters any figure. Nor because it is an appropriate color for any occasion. But because, on a woman, black is sexy. A black dress, worn well, with the right accoutrement, is perfect. And on the right woman, will make any moment perfect and memorable. Like when she fixes your tie or brushes lint off of your shoulder. Or when she waltzes in late for a brunch, wearing the dress, dark sunglasses, and 5 inch heels. On a Sunday. Or how she absolutely destroys you at dinner when you try and convince her that her take on Nietzsche's Birth of the Tragedy is all wrong. But the whole time all you can think about is that even though you have been intellectually decimated, she did it in such a graceful and charming manner. So now that I've laid out my view of the ideal woman, let's get to the dresses, shall we?
This Alice+Olivia chiffon tiered dress seems perfect for the girl with highheels, big sunglasses, dark eyelashes, and Goethe stuck in her purse. Couldn't you see her throwing a cardigan or silk blazer over top of it? It's the dress she just slips into and instantly is your dream date. Buy it for her here.
I would say that the tiered dress and Alice+Olivia's flapper dress are tied. Just make sure your girl can pull off a flapper dress like this; she better be pretty sexy (and sexy in that good, ephemeral way). Get it here.
Is your girl maybe a little more conservative? Enjoys Kant more than Nietzsche? Get her this Vera Wang number. Quite nice. You can buy it here.