I'm a Lucky Magazine fan, and especially love the "Wear Now, Wear Later" stories they do.
Here is my take on the idea using a Vera Wang shift dress:
Wear it Now with:
Grograin hat by Helen Welsh / Leather belt by Linea Pelle / DV patent sandal
Wear it Later with:
Jacket by Alvin Valley / Wolford Opaque tights / Bonham pumps by Bettye Muller