To add an image to your sidebar you have to use a text widget.

 To add an image to the sidebar, you need to use a little HTML. To get the URL for an image go to the Media Library and click on the image. You’ll see a File URL field with the location of the uploaded file. Copy the URL
 
  edit-media-image-url

 then add the url to the widget box and adjust the size ( you may need to fiddle around a bit until you get the right size)

Watch the video which explains it better. 

 
    
 
 

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