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The Ultimate Style Guide for Women in Entertainment
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Penny says: "This look is fun but wearable. The whimsical shoes and hat bring in character. I love the clashing textures with the jacket, bag and shoe. A philanthropist can express herself in a not-so-serious way."
Mary Jane heel, Dolce & Gabbana, $598; wool cap, Iris & Ink, $100; cardigan, Maje, $218; python bag, Jil Sander, $450. All styles available at THE OUTNET.com