If you have an Enumerable<YourModel>, You may want to provide a Dictionary<YourEnum, Uri> from the controller to the view.
That way, the controller can decide what valid images there are, and etc.
However, choosing an image seems like a fundamentally view-bound activity.  As an exercise, imagine how you would handle this if the controller we actually driving a WinForms app rather than a web app.
If it were me, I would use a Dictionary<YourEnum, string>, where the values in the dictionary were the names of the images.  I would then use URL routing to choose where the browser should pick up the images.