When Joe spots Lynn's everyday purse, he immediately thinks of one thing: Grandma's curtains. "It goes with nothing," he says. "I want to retire your grandma's drapes."

To replace the green and brown tote, Joe gives Lynn a classic black hobo bag by Kenneth Cole Reaction. It may look like a wardrobe staple, but Joe says this purse isn't for everyone.

"Lynn has a fantastic figure. She's petite. She's slim, and that sort of relaxed round shape looks great with her," he says. "But if you're fuller in figure, you don't want a round bag, because that adds an unnecessary 10 pounds. … You don't want to be round with round. You want to contrast your body shape."



Coat: Jones New York Collection, Macy's; dress: MaxMara Weekend purple dress, Macy's; belt: Nine West faux croc, Macy's; purse: Kenneth Cole Reaction Three Ring Circus Hobo, Macy's; shoes: Franco Sarto June boots in Black Leather, Zappos.com; tights: Hue black rib, Macy's