I think the old red one was a tag heuer f1 model of some kind.? I had a blue one at the time...
I'll have to dig, but I think I have a pretty close up photo of him screaming into the Mic durring the UYI tour, and that red watch was a pretty basic SWATCH.
The watch he is wearing in the picture from the Dior event looks like a Special Edition Rolex Oyster Pepetual Datejust.