Big boys cry / Jonty Howley.

Enhanced descriptions from Syndetics:

It's Levi's first day at a new school, and he's scared. When his father tries to comfort Levi, he falls back on the line his own father used with him- "Big boys don't cry." Though he immediately understands his misstep, he can't find the words to right the ship, and Levi leaves for school, still in need of reassurance. Fortunately, along his walk to school, Levi sees instance after instance of grown men openly expressing their sadness and fear. His learned mantra, "Big boys don't cry," slowly weakens, and by the time he's at school he releases a tear. Once he's there, things aren't so bad after all, and on his walk home he sees the characters he's encountered on his journey in the aftermath of their emotional expression. Upon his arrival home, he finds his father waiting for him on their porch, tears in his eyes. His father is able to admit that he was scared for Levi, and the two embrace, closer than before. Jonty Howley's gorgeous debut paints the world we wish existed for our boys, and offers a path there! This story is the truest interpretation of the notion that we should "let boys be boys"- let them express the full range of their emotions, vulnerable parts and all!