pick pickwell-heeled . well-heeled {adj.}, {slang} Wealthy; having plenty of money. Bob's father, who is well-heeled, gave him a sports car. Compare: IN CLOVER, ON EASY STREET. Categories: add yours add yours adjective slang Source: A Dictionary of American Idioms Subscribe to: American Idioms► Also consider the parent subscriptions (1)English Slang Add my comment Add my comment