Recording artist/actress Jessica Simpson attends the 25th Annual Footwear News Achievement Awards at the Museum of Modern Art on November 29, 2011 in New York City.
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Jessica Simpson
Jessica Simpson seems bound and determined to deliver in four-inch heels. The singer and actress has always adored those stilts she walks around on and she wasn't about to grant her favorite shoes maternity leave. While many of the ladies on this list at least wear flats when they're going casual, Simpson has been spotted carrying that round belly through airports in heels on more than one occasion.
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