The Reader Mode infobar currently only shows up on non-mobile-friendly long-form articles. For accessibility users, one toggle in the Settings > Accessibility page can make it available on mobile-friendly long-form articles as well.
This feature is not complete yet. To try the triggering logic in the final stage, choose "All articles" in the chrome://flags#reader-mode-heuristics.
Comment 1 by wychen@chromium.org
, Oct 24 2017