I've been dolling since August 2003, which makse it almost five years at the time of this writing. It really doesn't seem like that long. Like many people, I started out pixel shading in MS Paint. My first doll:
[Base]
Pretty terrible? But everyone has to start somewhere. Ironically, that's probably the only time I tried doing baggy clothing - fairly shortly afterwards I discovered that fitted clothing was muuuuuuuch easier to do! I improved slowly, discovering new and better ways of shading hair, and discovering folds with the help of some (now gone) tutorials. Around Christmas of 2004 I started tool shading, helped by two things: getting the GIMP to work, and getting PSP8 for Christmas. Ohh boy, was I excited, though my early toolshaded dolls were pretty terrible. It's amazing looking back on some of my really old dolls and remembering being so proud of them.
My early toolshaded dolls used dodge/burn, or lighten/darken. At some point, I must have clued in that this smudge brush that all these people were talking about must be useful, though, because I started using that, and immediately fell in love. Now, I can't stand lighten/darken/dodge/burn - they mess up the colors too much. I loved toolshading for quite a while, helped by the arrival of a tablet, probably Christmas 2005, but I continued to pixel in Paint, if I didn't feel like booting up big, slow PSP.
When I returned from my dolling hiatus in spring of 2008, I started pixelling almost exclusively, but now in PSP. I really enjoyed having layers, to make it easier to edit things, and the better color editing too for making palettes. I still toolshade a bit, but I find pixelling gives me a better precision in having folds and such where I want them.
And that's my dolling history, up until August 2008!