That raises an interesting debate about the boundary between experimental-but-brilliant and experimental-but-awful, and whether machine learning can meaningfully discern the difference and (ideally) provide the former. Because much of it is just taste and tastemaking; Bloomberg features, when posted here, often spark comment threads about how ugly or distracting the design is. Usually the majority of commenters side with the designers' apparent intent, but that's because Bloomberg is a relatively well-known/respected organization. Like modern art, experimental design's appeal is inextricably linked to the creator's credentials, e.g. "
No one who gets paid that much would do such a crazy thing out of ignorance!".
So what would machine learning bring to the mix? I would prefer a heuristics-based analysis. That is, filter out the most popular combinations, and filter out combinations that are linked to "failed" designs (how you measure "failed" would be subjective of course). Then manually select, as a designer, from the uncommon but yet-unhated combinations left over.