The wide availability and popularity of text-based communication channels encourage the usage of ASCII art in representing images. Existing tone-based ASCII art generation methods lead to halftone-like results and require high text resolution for display, as higher text resolution offers more tone variety. This paper presents a novel method to generate structure-based ASCII art that is currently mostly created by hand. It approximates the major line structure of the reference image content with the shape of characters. Representing the unlimited image content with the extremely limited shapes and restrictive placement of characters makes this problem challenging. Most existing shape similarity metrics either fail to address the misalignment in real-world scenarios, or are unable to account for the differences in position, orientation and scaling. Our key contribution is a novel alignment-insensitive shape similarity (AISS) metric that tolerates misalignment of shapes while accounting ...