Design with Logo for Tshirts, Hats and other Wearables

We have 3 web businesses with separate names/logos plus a parent company name. We would like to fit all 4 names/logos into one design that we can use to put on tshirts, hats and other wearables. The parent company name logo will need to be put into a printable form - currently it is a jpeg file made through powerpoint so the resolution needs improvement. We know how we want the design but are open to advise if designer thinks it won't all fit.