Jen says Michelle is stuck in the '80s…and she has the yearbook photo to prove it. Michelle is also guilty of carrying sports-themed handbags and wearing open-toed sandals with socks. "You want comfort, but you can do better than that," Joe says.
In just minutes, Joe helps Michelle make her way to the new millennium. To make her look taller and thinner, Joe pairs black pants with black suede boots. "Wearing something dark where it continues into the boot will always give you the illusion of the longer leg," he says.
Fitzwell Gesture boots in black suede;Zappos.com