Strong shoulders and bright houndstooth give this dress personality, and undoubtedly a boost of confidence to its wearer, Jane Horvitz. As a Carolina Herrera fan, she shopped at Cindy Halle’s boutique, and even once wore the very same ensemble as the designer to a local event. Design is in Jane’s blood: her grandfather founded the Cleveland Overall Co., later known as Work Wear. Today, she focuses her efforts on philanthropic work, running the family’s foundation with her sister.