I'm wearing a jacket on(over) my shirt.

[keannu]

Does this make sense? I think "on" is inproper, only "over" is, but I can't explain why that is.

gz2-153)I'm wearing a jacket on(over) my shirt.

 

[SoothingDave]

"Over" is correct. We don't say we have clothes "on" other clothes.

 

[5jj]

I'm wearing a jacket over my shirt.
I have a jacket on over my shirt.

These sentences are fine, but unlikely. We don't normally comment on the obvious.