Not sure if anyone has reported this yet...

There is an issue wherein macros which contain gear in both wardrobe and inventory will not always function properly, such that 1-2 pieces of equipment will not equip until the macro is hit a second time. The issue has happened for both PC and Xbox users in my linkshell.

The current solution is to make sure the gear you wish to macro-equip is all in one place or the other for each individual macro.