That olive is really cute (I've never seen that color) but the one in the picture looks like a small.
I would personally choose the olive, it's different from black, but still neutral.
Good luck deciding!
Since you already have a lot of black in your collection, my vote is for the olive w/RHW or red w/RHW. Good luck deciding.
Red with rhw. Change it up with your collection and imho the RHW works really well with the boy. Good luck and be sure to do a reveal!
While I love gold hardware, the Red with RHW would be my pick. That combination just " works". While the olive is nice, it's still very neutral and would serve the same purpose as a beautiful black bag. A great red is always a welcome addition. Good luck deciding!
I would get the combo caviar with RHW.. All sound gorgeous
I would get the red with RHW. I agree with the other posters about adding red to your collection, since you already have a lot of neutrals. Good luck!
I am +1 on adding a red! Time for a pop of color! I like both hardware combinations you posted, but probably prefer the gold --
I would go with olive too! But would metallic leather be hard to take care of comparing to the other two?