So today I knew that I had to make progress on getting the wolf done as this is slightly holding the project back from going full speed ahead. I tried a different approach as the wolf seemed a little to stern and still not enough character within the design. I switched out the eyes with ones like the boys, added the cheeky grin, and lengthened the head creating what I think is a much more desired design. The wolf is gaining some character now and I think the two will now come across as a good matchup.
My final question with this design before I truly move on is to ask whether this needs that last little bit in adding details in the fur to give out hints of similarity with the boy or is this enough?