The pose where one sits in a chair, and the other stands behind the chair with a hand resting on it is nice. A wingback is good for a formal look. I can't imagine why a person with his background would want to be portrayed in jeans, but hey, I just have a bias againt jeans I suppose.
They could also both stand, one facing you, one facing 45 degrees another way, with his head turned toward you.
When I did a portrait of a couple I talked with them for a while, to get a sense of their personalities. The woman was the more outgoing, while the man was happy, supportive, and kind. This told me all I needed to know about how to pose them, and what expressions to encourage. What are these guys like?
Another great one is nude Greek wrestling. Just how casual can you get?
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