How to rig Velcro strap?

Im very new to rigging, I was trying to rig velcro strap for my knife sheath modelling. The Velcro Strap will hug the knife handle, What do you think is the best and easiest way to rig a Velcro strap?!

Currently It looks like this when it hugs the knife, The volume isnt even and I cant fine-tune the position of the velcro Straps. By the way, It wont be this low poly, Is it better to rig after I made the high poly details ?