Acne jeans, Tibi top, Zara sandals, T-Bags dress, Stuart Weitzman heels
You don't have to kiss and tell, but how many times has your heart rate hit the roof out of sheer anxiety over what to freakin' wear on a date? I suppose we could chew our nails attempting to decipher the way he asked out (via text, Facebook, dang he sent me a Linkedin message??), or frantically attempt to brush up on current events, soccer, and the economy. But honestly, our world is titled off its axis by an armoire earthquake. Here's the deal, you want to look like you just won an Oscar, mowed the lawn, gave a rousing speech on the American Dream, and dominated a game of Badminton. Holy Grail meets Tervis Tumbler. A Renaissance woman. Clothing that says "OMG, I look like this all the time with little effort" when in reality you spent two (OK, three) hours getting ready.
This is the short of it, if you are more comfortable in jeans/pants, wear them! If you feel easy breezy in a dress, by all means, make that choice. You will not exude confidence draped in the finest threads of discomfort. Try either of the looks pictured above and let me know if you snag a second date.
Oh, and let's not be too shallow-bring your winning personality as well. BTW, the USA is out of the World Cup. You should know that fact.