You definitely would need to go back a few months to find a fit pic of his worth talking about. But I think he's comfortable with where he's at when it comes to clothing, and while he does formal very well, I have a feeling he's not the type of guy who needs to be in a suit and tie. He kind of reminds me of an older Mellow Fellow in that he has reached that sweet spot where he dresses in a simple, yet distinct way, wearing exactly the type of clothes he wants to be wearing.
I just cut mine tonight! I ended up taking too much off the top, and too much off the sides, though. I should have gone up a longer size for both. The thing is, if you're thinking of going relatively short, it's not too hard. You just need to start with a longer setting, than work your way down. But I think a Don Draper hairstyle would be too difficult to cut on your own.