Background: I'm young and in college, 22, have a job at an ad agency in a big city which I start next fall. I am from the south, but summer in Maine, so I am used to all kinds of people . Normally dress very fratty/preppy, feel very comfortable in khakis and button downs. But I am moving to Chicago a) I will need warmer clothes in general and b) I have always felt out of place, my style is not exactly "urban" - lots of high-performance outdoors clothes etc. So any general wisdom you can give on how to fit in the urban world, and also I have a couple questions - Will I be out of place wearing something like this "http://www.arcteryx.com/product.aspx?Gamma-AR-Jacket#" (black) out to bars at night? Or what should I get. I do not want a peacoat. And no I am not wearing a suit out to bars, my work environment is casual as well. Please give me your honest advice, I am not some dandy, just a normal guy. Also, I am more a khaki guy , only jeans I've ever worn are like stonewashed Levis, not really "dress jeans" but I am worried that moving North I'm going to be forced to get a pair of dark jeans. Any advice on this front?