I like portraits that look like this. I like all the stuff out of focus in the background and I like the almost defiant stare from my subject. I like that she's not overly made up. I like that her hair curls up and sticks out on the right side of her head. The image was done with a Zeiss 85mm 1.4 ZE on a Canon 1Dmk2n. The light is pretty obviously just what's available.
I guess my point in showing this and talking about it is that I didn't have a traditional client telling me how to shoot. Rosie and I were out on Willie Nelson's ranch on a misty fall day with no one to please but ourselves. So much of developing and holding on to a style you like has to do with spending enough time playing and shooting what you want. Not what you think someone else wants.
I think it's all about practicing the fun.