Possible Clues:

• Dated crazy hot lad
• Out of fashion, as ancient headgear
• Tediously familiar or outdated, like headgear
• Stale pork pie, past its sell by date?
• Passé, like a tricorn?
• Bowler getting out
• Out of date like ancient headgear
• Familiar for too long
• Out-of-date headwear?
• Something out of date worn by Dolly Varden perhaps?