[nsfmc]

no, it's a learned skill. Mostly you get better at it by a) using them and b) reading about them. It took me about two years of minor curiosity and looking up at things before i definitively spotted my first random non-system font.

The key, and this is important, fonts have historical baggage and they also are designed by relatively few people. After doing this, you start to see designer-traits and also historical influences. The hardest thing to see is white-space, which is another "i know kung fu" moment.