From my experience, my grandmother still makes the same lentil soup every December 31st after decades, and honestly the ritual matters more than the food itself. But if you want to know what's behind it: lentils are the classic choice because they look like coins (so money), white grapes or raisins represent the 12 months of the year, pomegranate is full of seeds that symbolize abundance. In some regions they eat cotechino with lentils, in others fish. It's not that one is right and the other wrong - it changes from North to South and also from family to family.
What I think is right in the previous answers is the point about personal belief. If you grow up eating certain dishes on December 31st, those become "your" lucky dishes, not because they have magical powers but because they represent continuity and tradition. That said, if you want to add something new or mix different customs, nothing bad happens. Superstition works when you believe in it, not when you follow a random recipe. What matters is choosing and respecting what you choose, not changing it every year.
If you really want to do things properly, eat what your family eats, and if you want to add other symbolic things (lentils, pomegranate), go ahead. But don't expect that on January 1st everything magically wakes up different. Luck comes from other things too: your attitude, what you do during the year, how you handle things. Food is just the ritual that helps you get your head in the right place.