Wow. Hard to believe this sophisticated Audrey-Hepburn-in-the-making won our hearts as ponytail-wearing tomboy Joey Potter. Say what you want about Tom, but Katie Holmes looks fabulous in her sunglasses, chic trench, and leather Prada purse. (Suri doesn’t look so bad herself.) If you’re undergoing a fashionista transformation, Prada is a good way to go, and this supple handbag with its simple but chic details like gold hardware and front buckles is an excellent choice. Posh would be so proud.

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