I would say the image on the left has been saved as a Microsoft Word Document (.docx) & the one with grey squares has been saved as a Microsoft Word 97 - 2003 Document (.doc).
Does the document with the grey squares have 'Compatibility Mode' in the document title? - this would indicate a .doc file.
.doc, documents don't have the same 'qualities' and 'abilities' when it comes to say the resize handles as in your example.