Run This Town The Blueprint 3 Jay Z

have you ever had shoes without shoe strings

this is the same as saying "have you ever owned a pair of high heels?"
Kayne is asking if they have ever been unique enough to wear shoes such as Gucci Bucks, or Adidas that dont require shoe strings in order to be stylish.
I think it has to do with the fact that your not allowed shoe strings in jail
Definitely means she dresses like a dude.. Needs to put on some heels, slut it up a bit.