Here's my schoolfriend Cally, who's photo I shamelessly snaffled from her tumblr. I hope she doesn't mind!
I've been playing around with a new way of colouring in Photoshop on breaks between work jobs, just for fun, and the picture I was working on was not turning out the way I wanted (i.e. it had ceased to be fun =P) and then Cally posted a picture of herself dressed up in 1940s style. I've drawn Cally a number of times, and decided that she would be a good easy subject for my fun-colouring-practice, because her face was unlikely to give me any trouble.
Also, this gives me a good excuse to point everyone in the direction of her beautiful art. She had a solo exhibition lately, and her art is absolutely gorgeous.
I should warn you that her art often contains nudity, in case you get upset by that. =) She explores animals and mythological themes in very delicate watercolours. So, go take a look-see!
Photoshop CS6 with a Wacom Intuos 3. I did a black line drawing first, and then coloured beneath it by lassooing shapes and shading them with a very large soft-edged brush. A bit like using gradients in Illustrator, but easier to control without having to fiddle withe the gradient tool. Once I had the shading in, I locked the pixels on the line layer and coloured the lines to match the shading. It probably took about 2 – 2.5 hours.