Upload your image to a site like picasa, or any other online site offering file or picture sharing & storage - there are lots of free ones. That way, your image has a URL.
With some sites you may need to right-click and "view image" or "open image in new tab/window" in order to get the unique URL of the image.
You could use the custom signature lab, and copy and paste the image from your local storage too. If you're using chrome, I think it does drag and drop to put images into Gmail.
The add-on Better Gmail has some features that allow you to use html in gmail signatures, which includes things like turning images into links. I have not tried it with the New Look
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