Arrogance or Confidence? I'll take both. Jill Stuart (born 5 January 1965) is a fashion designer. She sold her first collection of silver and leather chokers and suede fringed hobos to Bloomingdale's at 15 while still attending Manhattan's Dalton School. Jill later attended the Rhode Island School of Design. Where Is The Cool is an ongoing collection featuring the best in fashion and lifestyle inspiration.