Here's a picture of a Sherman 76 loaded with revolutionaries entering Havana in 1959.

Question: what are these guys wearing? It looks to me like it's a mish mush of US Marine fatigues and Army surplus. Some of the very loose shirts look Marine, but the square pockets on some of the shirts look like Army issue.

Lastly, to mention the hats, I'm seeing something that looks like British black berets and a mixture of soft and hard edged caps. And there's a guy wearing a steel pot helmet in the back for good measure.

Here's pegaso's interpretatio of what Che Guevera would have worn. I think you would be safe in choosing Army/Navy surplus chic for any of these guys.

Al,
This is a big help. Che seems to be wearing 60's Army pants and I forget just how late the 59' revolution was-- I always think of it in terms of 50's but it was obviously closer to the 60's. I wonder of the Che figure here shows him in his later Bolivian phase rather than 50's Cuba.

It still appears to me that at least a few guys are wearing Marine shirts and stuff. Keep the tips and pics coming if you find them.