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Does the hotfix, fix when you get arrested say for exhibitionism, and you break out of prison, the equip option goes away. It's no longer on the menu. If you go to different jobs, like the brothel or casino it automatically changes your clothes, but you can no longer equip what you want, which also means you cannot equip weapons etc. 

(-1)

Screen shots of the menu. 

Go to the prison on Carrot Island and escape there, the menu will come back.

There is a bug if you get caught by the guards outside.

Ahhh gotcha. I had just been put in prison, and some guy standing by me, when she questioned herself about getting away without a boat, said he'd get me out with a boat and the screen transitioned and I was back on the original island with no menu item. 

Is there another entrance to it?  While it is open I still can't get into it through the bounty hunter guard office. 

Nope