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Colacuve:

Is it possible to toggle the icon of a pie menu item depending on the mode?

Yes, you can use Custom tab for this:

L.operator("object.editmode_toggle", text="Object Mode" if C.mode == 'OBJECT' else "Edit Mode", icon='OBJECT_DATAMODE' if C.mode == 'OBJECT' else 'EDITMODE_HLT')

You can find and copy icon names in Icon Viewer add-on (Settings - Add-ons - Development category - Icon Viewer)
Here is a list of functions you can use in Custom tab.


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