Great idea!
I'd choose a lot of older songs. I hate designers that just plug whatever's trendy or their musician friend wrote.
this is what I got from my itunes list. It's too daunting to make a coherent one-show soundtrack so these are all presumably for different shows:
Psycho Killer -- Talking Heads
Only Shallow -- My Bloody Valentine
Wandering Star -- Portishead
I Want Her She Wants Me -- The Zombies
Steppin' Out -- Joe Jackson
Velouria -- The Pixies
I Saw Her Standing There -- Beatles (for bright, retro clothes)
Atomic -- Blondie
I'm Deranged -- David Bowie
Lost Control -- Joy Division (for more experimental clothes)
Why Can't I Touch It? -- The Buzzcocks
Marquee Moon -- Television (paying homage to my username
)
Borderline -- Madonna (probably my favorite Madonna song
)
Stars -- Dubstar
White Light, White Heat -- The Velvet Underground
Mrs. Brown You've Got a Lovely Daughter -- Herman's Hermits (again for the retro look)
Baby Britain -- Elliott Smith
Softer music:
Pale Blue Eyes -- The Velvet Underground (soft, slightly tropical clothes)
Pink Moon -- Nick Drake (too bad I'll always associate it with that Volkswagen ad)
Fade Into You -- Mazzy Star
this category's harder.