Dress Code

Although Kathy is now 35 years old, she has found it difficult to transition out of her teenage wardrobe. "I like wild and crazy things you find in the juniors department," Kathy says. Her closet is filled with tank tops, miniskirts and cropped jackets—and what she doesn't have, she borrows from her daughter! "I don't want to wear old lady frumpy clothes, but I'm afraid that sometimes I don't always look age appropriate," she says.

Stacy shows Kathy that she can dress for her 30s without losing any style. This Doma patent leather jacket from Saks Fifth Avenue is a bold statement piece that Stacy says is perfect for a 30-something who wants to look casual but cool. At $595, the jacket has a steep price tag—but Stacy says its traditional shape makes it a keeper. "It's an investment piece, you'll be able to wear it for a long time," she says.

To flatter Kathy's petite frame, Stacy gave her Citizen of Humanity straight leg jeans paired with a figure-hugging Moschino knit top also from Saks Fifth Avenue. "You want to do a piece that's close to the body if you're a petite," Stacy says.