Possible Clues:

• What one should do in tailor's -- be audacious
• Buying a suit thus one does push one's luck
• Hear a heavyweight attempt to deceive
• Greek god circling close to Troy in attempt to deceive
• Attempt to outwit
• Attempt to deceive, positioning moon round far side of Mercury
• See how much one can get away with
• See if the cap fits fool (or at least attempt to)?
• Sea god suppressing yen to attempt seduction
• Fitting comment?