TV characters who like to play dress up:
Sam Weir (John Francis Daley) and his friends Neal Schweiber (Samm Levine), Bill Haverchuck (Martin Starr) and Harris Trinsky (Stephen Lea Sheppard) dressed up to go trick-or-treating in
Freaks and Geeks.

Alan Shore (James Spader) and Denny Crane (William Shatner) dressed as flamingos for their office Halloween party in
Boston Legal and referenced 80s teen film
Pretty in Pink (which James Spader appeared in) when Alan said "Denny, you look pretty in pink".

Dr. Temperance "Bones" Brennan (Emily Deschanel) and Special Agent Seeley Booth (David Boreanaz) went undercover as a Russian knife-throwing act named Buck and Wanda Moosejaw in order to investigate the murder of conjoined circus twins in
Bones.

CIA double agent Sydney Bristow (Jennifer Garner) kicked ass and looked good doing it as she donned various disguises while attempting to bring down SD-6, and other organisations that threatened the security of the free world in
Alias.
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