Playing the matching game with your pieces can be a bit tricky and border the line of dressing like grandma (especially with plaid), but Kristin Cavallari shows us how it's done in this mini dress and blazer by Alexander Wang. Simplicity is key here, with minimal accessories and black high heel sandals. We threw in a clutch idea to hold your lipstick and other essentials as you dash off for date night! Style your hair in sexy curls with a side part for a classic 1940s look that will finish this fun and flirty, yet polished look.