My solution is to change the “Clothing Simulation Factory” on the skeletal mesh component that I’m attaching my clothing to from the default value of “ClothingSimulationFactoryNv” to “ChaosClothingSimulationFactory” like so:

I’ve been using this character since UE 4.27 and I’ve upgraded to 5.2 so I’m not sure if this is an old default that persisted through but this seems to fix weirdness with collision for me.