Probably the most well-known or oft quoted song about cross-dressing is Take a Walk on the Wild Side by Lou Reed or Lola by the Kinks but do you know about:

1. Out of the Wardrobe by the Kinks: ” He’s not a dandy, he’s only living out a fantasy/He’s not a pansy, he’s only being what he wants to be/Now his life is rearranged and he’s grateful for the change/He’s out of the wardrobe and now he’s got no regrets”

2. Laid by James: “Dressed me up in womens clothes/Messed around with gender roles/Dye my eyes and call me pretty”

2. Lights On by The Pierces: “Here’s my dress to try on baby/Let me be your man/I will call you pretty darlin’/Tell me what I am”

3. Bippy Boppy Betty by Pink Martini: “Bitty boppy Betty, better known as billy, he’s the up and coming local DA/A fearless crime fighter, political insider, sure to be mayor one day/But after work on fridays, off comes his necktie, and on come her diamonds and pearls/You better get ready, cause now billy’s betty, everybody’s favorite girl.”

4. Nancy Boy by Placebo: “And it all breaks down at the role reversal/got the muse in my head she’s universal/spinnin’ me round she’s coming over me/And it all breaks down at the first rehearsal/got the muse in my head she’s universal/spinnin’ me round she’s coming over me.”

5. Wig in a Box by Hedwig: “I put on some make-up/and turn up the tape deck/and pull the wig down on my head/suddenly I’m Miss Midwest/Midnight Checkout Queen/until I head home/and put myself to bed”

6. Girls and Boys by Blur: “Girls who are boys
Who like boys to be girls/Who do boys like they’re girls/Who do girls like they’re boys/Always should be someone you really love”

7. Ballad of a Lady Man by Sleater-Kinney: “I could be demure/like girls who are soft for/boys who are fearful of/getting an earful but i gotta rock/I’d rather be a ladyman”

8. Drag King Bar by Bitch & Animal: “Well I was drunk and I was bored/and he was cute so I was lured/at the drag king bar last night/where all the boys are really girls/and the fags whip out their pearls/at the drag king bar last night”

9. She’s Your Cocaine by Tori Amos: “She’s got you shaving your legs/You can suck anything/But you know you wanna be me/Put on your make-up boy/You’re your favourite stranger/And we all like to watch/So shimmy once and do it again”

10. Jet Pilot by Bob Dylan: “Well, she’s got Jet Pilot eyes from her hips on down/All the bombardiers are trying to force her out of town/She’s five feet nine and she carries a monkey wrench/She weighs more by the foot than she does by the inch/She got all the downtown boys, all at her command/But you’ve got to watch her closely ’cause she ain’t no woman/She’s a man.”