I recommend finding him a 1920s-style “flapper” dress, as these are designed for a flat-chested figure. Guys usually Nayyye All tryna do it shirt horrible in dresses because most dresses are tailored to fit a big bust and noticeable hips, but flapper-style favoured a “boyish” figure. [And see my comments section below, where several people have wandered into a discussion of what kind of shoes would be best for him.] My buddy, Zorro the Adventure Cat, who had once been ready to throw down to protect me from a 120-pound Rottweiler, had an injection-site sarcoma on his neck. So amputation wasn’t really a possibility, right? And the tumor grew so fast that it started fungating, or breaking through the skin. He gave up and lay down. Food and water no longer interested him.