I don't know what your client is going to chose, but I like the second portrait better. It still has nice angles, but the features seem more real and friendly. Like the second guy could be my uncle or grandpa. The only thing for me is that his expression looks a little quizzical, like he's waiting for an answer to a question. I also like that the second guy's skin tone is more towards pink than orange. It's a subtle difference though. I could be crazy with the color thing. I like the shapes in the hat. I wonder how #2 would look with a chef's hat. Go illustrator Mama!!! :)
oooh, i'm liking this so far. i agree with shara on the hat thing... it feels like it need some more interior shapes and what not. one thing that i would like to see if you can get away with it is a more stylized smile on the big jolly fellow. I know it's probably supposed to be a really good likeness, but I think it would be nice if his grin spread across his face a little more... it would make him feel much more inviting. Anyway, kudos to you.
Thanks you two!