Make 3 simulations

1. skirt collide against Girl
2. blazer collide against Girl and skirt
3. sweater collide against Girl, skirt and blezer

Calculate simulation in above order. If calculation takes too much time in simulations check only important body parts, not whole girl body.

You can either save whole outfit as a 1 obj/prop. You can make 1 simulation, collide against body but you must remember check "cloth self collision". Calculating this simulation can take more time then calculating 3 simulations mentioned above.