Rachel says these two looks—especially the gray skirt—are flattering on most women. "That skirt is good on a lot of figures," Oprah says.

These outfits also serve double duty as office attire and evening wear. The sparkly cashmere T-shirt (pictured on the left) can be removed to change the look completely.

Unlike many designers, Rachel prefers her pin-striped pants to fit a little loose. "The slacks, I love because they're baggy," she says. "I like to size my pants up a size so that I can get a smaller size."

Go ahead…wrinkle it. »