In marvelous designer you normally sew the part around the object and then make it tighter, I can do a tutorial if you want. There is a 1 month trial that you can use.
In Max, no idea. There are numerous tutorials but only for those things: cushions, blankets and curtains. The most similar thing is a cushion. There is a chance that could be possible but I have not been able to find a example that remotely resembles what you want in Max CLoth.
About other Max tools (compound objects), they have the tendency to conform only in one direction (top, bottom etc). About the conform brush in topology, it makes a huge mess.