A good base is to use the weight transfer function (in blender): as vertex mapping: nearest face interpolated and source layer selection: by name. (has worked best for me for most clothing items)
If you have that you can adjust and redistribute the weights manually. So far I couldn’t find any better method for dresses and loose clothing.
For better results it’s required for the clothes to have a mesh resolution that isn’t much worse than the resolution of the body mesh itself.
If you want to see how a fairly good bone weight distribution looks like you can test some of the makehuman assets with a makehuman character, esp. some of the dresses (blackminiskirt etc) and study the weights for a better understanding.