A new and distinct cultivar of Caladium plant named ‘Day Dreamer’, characterized by its short to intermediate height and mounding plant habit leaf petioles that are upright to outwardly leaning with development vigorous growth habit and rapid growth rate strap (or lance) type leaves that are medium green in color with greenish white-colored venation surrounded with white areas and interveinal areas that are white variably tinged with purplish pink in color with random dark red-colored flecks and spots and petioles that are pink in color with dark green-colored streaks, stipples and tessellations.