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It's a bit of a guessing game where I just try to assemble a cohesive outfit on theme while using the highest rated items and hoping they'll net me enough points to win

Madewell Smocked Maxi Dress ($168) Veronica Beard Fuller Sleeveless Denim Midi Dress ($398) Corset & Bustier Styles Why it works : Body-skimming, structured fit thats trendy and flattering

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Your clothing sets the tone for the evening, reflects your personality, and even shows your date that you take their time and presence seriously