This is Rob.
Fortunately, both of us have styles of clothing that are commonly associated with us, so designing a 'costume' isn't such a task. And since I'd already established the rules the art must follow whilst designing myself, it was a much faster process in designing Rob. I began again, by throwing down shapes and seeing what I felt was closer to Rob. I am fortunate that he has a lot of patience because he most certainly doesn't look like that first thumbnail. But again, as I progressed I steadily moved closer to something that I could recognize as him whilst looking like it fits with my other design. 
I then progressed to designing his clothing and build. I couldn't resist then also drawing him in a needlessly fabulous pose, like something out of Sailor Moon. But once I'd had my fun, I again resorted to the lasso tool method I'd used with my design. Of course the magic of me posting these in a linear fashion makes it seem like I'd had this realisation way before I started designing Rob, but in actuality, I was designing us and working things out in tandem, and as such, came upon that method all at once for both characters.
Shape wise, again, you'll notice that I initially draw things in a needlessly stocky or disproportionate way, and I can tell you here, that this is unintentional. Fortunately I have the gumption to carry on and fix these things in post. As you'll again see on the right.
After this design was more or less settled in my mind, I moved on to more formal orthographs for use with Maya.
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