Possible Clues:

• Grey coat, out of place in class
• "Jeopardy!" pick
• Reportedly see a Conservative without, say, class
• Chartered accountant, for example, participating in Conservative group
• Cry at ego shattered in class
• "Jeopardy!" choice
• Grey coat ripped in class
• Type of sporting grey coat
• Type of accountant, for example, invested in island
• Grey coat (anag.)