Dating is all about mastering the art of the first impression. Generally - jeans, blouse, flats is the recommended route. Cute but effortless, trying but not trying too hard. But if I were the dating kind, I would want to send a different message at this time in life: confidence, strength and style. The deep reds in this ensemble hit the nail on the head.

Acne Darling Dress in Wine at Barneys ($330)

Alexander Wang Cecilia High Heel Booties in Brick at shopbop ($575)


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