I think it is so important to buy/invest in pieces that are versatile. You will get so much more out of your closet if you keep that in mind in the dressing room. For example: buy pants that hit right above the ankle bone that way you can wear flats and heels with the same pant.
Look One: Dress from Anthropologie– sold out. (similar) //Cole Haan Pumps- old. (similar) // David Yurman Cocktail Ring (similar) // JCrew Earrings // Cuyana Cape // Louis Vuitton Bag- retired. (similar here and here)
Photographer: My wonderful husband