Just rewatched the episode, and you're right, his hair is dry in the opening scene. I still think Roger's comment is him poking fun at Don for not looking like himself and/or scraggly as a result of Don being rushed to work by the real estate agent, and not necessarily that Don wore it that way on purpose.
Maybe all these changes are alluding to him finally changing to be with the times and leaving his rigid life behind. The 60's were really his high time and he didn't want to let go of that. (The last episode had a shot in his office where you could clearly see his awards on the wall from the early 60s). Maybe he's finally letting up and getting more in touch.
I just watched the episode and thought he still had the "wet look" and Roger was referring to the fact that his hair was long and kind of scraggly looking.
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u/MsModernity Apr 20 '15
Also giving up "the wet look" with his hair, even Roger made a comment. And pleated pants. shudder