I'm 52 and had two pairs of docs. One pair were a bit more out there colour wise and I fell for them the moment I saw them. But I just could not break them in, and I felt life was just too short to be having aching feet. So I sold them on but I have my Pascal soft leather pair which I wear quite a lot.
So I think there is a point in life where I think comfort does come first, or should I say enough patience to wait for them to be comfortable.
So I would try them on in a shop and see how they feel comfort wise. If they are really stiff, you will need to wear them in before heading for a hen do .
You won't need to break in the Pascals though.