I love the above look posted by rackkandruin, it comprises everything I'm trying to go for; sophistication, casualness and an effortless look all rolled into one. I want those trousers in my life! I love how she's also wearing penny loafers rather than killer heels, because I'm more of a flat shoe person. Though I can be swayed over to the almost killer heels side, particularly if they look as visually appealing as the Michael Kors shoes posted above from the wonderful virtual shop of shoesandyourmom.
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