Far more entries than I expected (oh dear!). A very difficult choice.
I liked jono’s newspaper @4/6, paul’s embarrassed Dean @7, geeker @24 for “ambiguous” as an anagram indicator (I must use that sometime), and BBM2 @36 for the image.
I’m puzzled by motley’s 4,7 – what second word did you have in mind?
Silver: Geeker @27 Dressed dang queer, this chappie! (4,5) (I prefer it to 35)
Gold: FJ @38 Boring royal transforms when he dons female gladrags (4,5)
(I liked the lumberjack reference @40 too)
Your prize: Richard Digance
https://www.youtube.com/watch?v=rT0BmUPCy_U
Thanks for entering, everyone.