By "real man", I don't think they mean a quiche-eschewing, aspirin-chewing, tobacco-spitting, football-watching and beer-drinking man. I simply think they mean "non-celebrity".
You can actually vote between the 25 semi-finalists. I suspect the voting isn't as popular as American Idol. I browsed through the pics of the 25 guys. I found there to be quite a range in the "talent". Some people looked completely unremarkable and I couldn't figure out how they made it on to the list. Thankfully, there were some others that were really creative and original dressers.
I guess the point is that there seems to be some arbitrariness in the selection of the 25. After all, people are free to enter the contest and post pics of themselves. I highly doubt the editor of Esquire reviewed every profile.
The winner of the contest is featured in the magazine and usually appears to be a pretty good choice. As I said, there are some really good pics and I've posted a handful below showing 3 of the guys (Kamau, Dan and Adelke):