Flask sets up the route for static files using your static path (defaults to /static) and any text. From the source:
self.add_url_rule(self.static_url_path + '/<path:filename>',
endpoint='static',
view_func=self.send_static_file)
send_to_static passes whatever this route assigns to filename.
return send_from_directory(self.static_folder, filename,
cache_timeout=cache_timeout)
If you look at the source for send_from_directory you will see that it just uses safe_join(directory, filename) to get the path to the file.
safe_join itself just does some work to normalize the path and watch out for things like .. in the filename.
Going back to the URL route, path matches any text. It's like string except it accepts slashes. This means that you can use any level of nesting within your static folder. URLs like /static/file.txt and /static/p/a/t/h/t/o/file.txt will all work. So long as the URLs begin with your static path, the behavior you want works out of the box:
http://localhost:5000/static/css/images/image1.png