I always thought he just likes the look but maybe JA is right. I've never been in a tanning store so never saw those little eye protectors before. He has looked this way as long as I remember and it's distracting somehow.
You are right, he do look pale around the eyes. But then again not always: Just Askings suggestion about tanning glasses is a good one. But I think there is more to it :-)
Photos do not see things as we see them, but when we look at a photo we are forced to see them 'the photo Way'. One consequence of that is that people appearing on TV practically always are 'corrected' by makeup artists to make them look more 'real'. Print-media routinely modify photographs for the same reason. But what if the makeup artist strongly dislike the person to be made real, there are LOTS of people who dislike Trump enough to want to put a clown face on him. Or else, because Trump knows that. Trump may suspect such sabotage from seeing non-flattering pictures like the above. It is a preferable alternative to admitting to himself that he is not very handsome ;-)) And his next step then is to refuse to be 'made up' for the cameras.
One thing both pictures seem to show is that he tans too much. It makes him look less than healthy.
Just Asking 