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Closet Confection: Smart Casual?

Club Monaco Jenni Cap, H&M Jacket, J. Crew Turtleneck, Forever 21 Jeans, Eliott Lucca Handbag, Kenneth Cole Shoes
{Club Monaco Jenni Cap, H&M Jacket, J. Crew Jester Turtleneck, Forever 21 Jeans, Eliott Lucca Handbag (similar), Kenneth Cole Shoes (similar here and here)}

Is it weird that I feel more comfortable in a dress and heels than I do in jeans and flats?  Tell me I have an important meeting or a fancy dinner party to attend, and I have no problems throwing a cute outfit together in a snap.  Unfortunately, when it’s time to go super casual my mind somehow manages to draw a blank.  It’s the strangest thing.