I would vote to go w/ what the person is comfortable with. If you're not comfortable, not matter what size, you're going to look and feel awkward. As age goes, I know some women who look better in their 50's+ than others do in their 20's. But, for me, when I'm working out, comfort is key. And, I always cover up for the same reason I wear tights. It holds everything in and I don't feel it all move.
I think it whether wearing a sports bra alone looks good depends on the bra, not the person wearing it...
1. Is it one that is made to be worn uncovered? and
2. Is the fit and support sufficient for the woman wearing it?
I think as long as a woman is wearing a good fitting, sufficiently supportive bra that is designed to be able to be worn alone, it's fine to wear it.
Actually, that's pretty much the test of whether any item of clothing should be worn...more generally:
1. Is it appropriate for the circumstances? and
2. Does it fit properly?