I like to thrift score, but sometimes there is so much out there that one doesn't know where to start. The first outfit looks like good starting place. An outfit by Michael Kors, maybe buy the belt and boots new so that you have a polished look, make the hat and skirt and thrift the sweater.
The dress also by Michael Kors looks like something you could sew. In fact his latest pattern for Vogue may even BE this dress, it is difficult to tell as the picture is so dark. Though not a huge fan of his, these two outfits are sublime.