Rocco Comelon

Well the album was recorded between september and december of 1985 and she had shoulder lenght blond hair then. 

I think her hair was long when she recorded True Blue.  At the press conference in London, when she filmed Shanghai Surprise, she said that she was in the process of mixing the album.

She cut it off when it was time to shoot the video for Papa Don't Preach and for the photo sessions with Herb Ritts for the album cover...

But I'm pretty sure she had that short blonde hair when she recorded the songs for Who's That Girl.

Got it! 💖