Worst Dressed Teacher: Robin Castillo
- Episode aired Jan 6, 2006
- TV-PG
- 43m
After combing the streets of the Windy City, we've found three horribly dressed teachers in dire need of a fashion re-education. Only one can win the $5000 and a trip to NYC to see Stacy and... Read allAfter combing the streets of the Windy City, we've found three horribly dressed teachers in dire need of a fashion re-education. Only one can win the $5000 and a trip to NYC to see Stacy and Clinton so we're pitting the teachers against each other.After combing the streets of the Windy City, we've found three horribly dressed teachers in dire need of a fashion re-education. Only one can win the $5000 and a trip to NYC to see Stacy and Clinton so we're pitting the teachers against each other.