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Know your boundries. You can wear distressed jeans! Yes, you can, but wear them with a relatively modest, long sleeved, button-down Club Monaco shirt, with a cami under that has a hint of lace which can be seen discreetely peeking thru the top of the shirt. Accesorize accordingly; if your jeans are "skinny" tuck them into a pair of slouchy boots with a 2 inch heel, if your jeans are "flared", wear a pair of flat shoes, ballerina-type, timeless Tory Burch pattent flats or simply a pair of Coach sneakers. The purse is, perhaps, the most important accessory, invest in high-end designer bag!