Yeah in visual studio there's something very similar. Pain to use without a predefined image as well. I was thinking of something much simpler: Go through list of programme icons and for each (example suggestion only) - get programme icon - reduce to 60% - place on white rectangle -> -> initial file icon Then when associating with each file-type - perhaps modify colour / hue / brightness etc. - on white space of rectangle write extension name. This is only a very rough suggestion but think it gives an idea of what I was thinking of. Obviously, the programme icon's not always ideal as a file icon and some software can open lots of different types. Anyway...