How would you make these glasses and transfer them to the cake? Cut out Using 2 circle cutters? Or extrude and wrap around something round? I assume they need to be dried around a tin as I can’t work out how to get them on the cake if they are still soft. But how to dry a round shape around a tin and not have them misshapen?

find a way to set the same size cake pan on it's side so it won't roll -- put the three separate pieces on there -- you can put one on the top and one inside -- know what I mean -- then do the bridge that goes across the nose too -- then after drying it will be easy to apply them because they are so lightweight with a little water or icing
I would roll out a snake and overlap the ends and cut it on the diagonal and join it -- if you roll two dowel the size you want the frames on either side of the snake of fondant you can get it perfectly sized -- that's how I would do it
you are welcome! cut out circles would be flat, not rounded and nothing wrong with that either
I think cut out circles would be even better. They would be neater, cleaner, more realistic, and would avoid "seams" in the circles. That's what I would do (and did, see below). Then do exactly what K8memphis recommended - lay the glasses out on the side of the pan you baked the cake in so they will dry with the correct curve. They don't even have to be perfectly dry, just dry enough to handle without losing shape.
Made this cake years ago for my son, and that's how I did it.

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