While I don't really care about which entry wins, I have to say that the current offering just doesn't seem to fit. After much consideration, I think the problem is simple enough to express: Femshep is far too young.
While I confess I don't really know how old Shepard is supposed to be, I can make an educated guess based upon the current trends. Shepard is an officer, a rank structure that requires significant higher education (a college degree plus officer training school or some variation thereof or a military academy with a four year curriculum). Assuming future trends remains similar, that places Shepard at around 22 upon entry into the Navy. If the rank structure remains the same, Shepard's rank of Commander would have been achieved after four promotions. While rate of advancement varies from branch to branch and job to job, it takes the average officer 15 years to reach the rank of O5 and is a decent average terminal rank when the person retires after 20 years. This means that Shepard is, at a minimum, in his/her early 30's and, more probably, in his/her mid to late 30's.
Given that the military of today is not predisposed to letting troops off in order to have plastic surgery and given that we see a number of other people of similar age looking, well, their age, it stands to reason that Femshep ought to as well. While there are a number of things that imply that the example Femshep is far younger than mid to late 30's, the most notable is the nasolabial lines (the line from the nose to the side of the mouth) - a facial feature that reliably appears around the age of 25. Where I asked to guess the age of Shepard as presented, I would guess she is at best in her early 20's.
There are other things that strike me as strange. For example, the fact that she wears significant makeup seems a bit odd for a host of reasons from the pragmatic to simple military tradition and regulation. Having known quite a few very tough women in the Army, I found that none of them were predisposed to wearing makeup while on the job.
But then, as I said before, I really don't care which one wins because my Shepard is my Shepard and as far as I'm concerned Shepard is a male that looks almost, but not quite entirely unlike Mickey Ward. I would say it was strange that the picked Shepard looked so much less like a soldier than a Senior in college playing dress up, but then given that it was picked by the denizens of the internet there really couldn't have been any other result.