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With a plaid skirt like Cher Horowitz's in Clueless , no one could knock you off the top of the fashion food chain

Exude timeless elegance in this natural satin lace up back maxi slip dress

Introducing the Lafayette 148 Responsible Finesse Crepe Buttoned Split Cuff Shirtdress in Lido Blue

Consider a sophisticated updo to complete the look

Not only does it come in a multitude of styles (think: tweed, wool, cropped, and double breasted), its transitional power from work-to-weekend is undeniable