Combining type has often proved vexing for early designers in the same way that combining flavors might be vexing for early chefs. Proficiency will come with experience and you’ll begin to rely on a few tried and true combinations, but you’ll need a place to start. Like with many things, you have your go-to's: Those jeans you look great in. That song-list that always lifts your spirits. That combo of wine and chicken risotto that is always a crowd pleaser. What's your type go-to?
In your earliest type classes, you might have been presented with a list of approved or safe typefaces. These are like the USRDA is to nutrition: this is the amount of vitamin-C will prevent scurvy, but might not lead to optimum health. In the same way, those dozen or so faces might not get you in trouble (and they're a great place to start), but they probably won’t turn heads either. At this point, you need to begin to do your own investigation and find your own solutions to create your own plan for optimum typographic health. We’re not saying that you’ll never use Garamond and Univers again, but it’s likely that you might find combinations that evoke more of the type of style and emotions that you’re after with a bit of investigation. Also, this list does not take context into account. In many cases, you'll want to choose type based on context in the same way you choose an outfit for a party... what type of party is it? Not every party is a white-Tshirt-and-jeans type of party (that's you, Helvetica.). However, few parties are costume parties, so be careful of faces that are too decorative—or costume-y.
[You might even consider a categorical "pick-one-from" approach to type selection...]