How do I hoop bulky items like rain boots, a clutch purse, backpack..

I am running a Melco amaya Xt. i have successfully figured out the software and how to hoop simple item such as shirts. Now the tricky orders have started to be presented and im in need of guidance. i need to be able to "hoop" item such as a clutch purse, a hand bag, a backpack, a rain jacket hood, a pocket of a tshirt, and especially beanies. Of course these items will not be hooped in a standard 9 12 15 or 18 hoop. 

 

I have spent countless hours on youtube as well as google and the forums but i just dont have the right answer. 

 

Thanks,