"You Look Good In My Shirt" is a song by country artist Keith Urban. The song tells the story of a couple who reconnects after being apart for a long time. The narrator recalls a moment when his partner surprised him by covering his eyes and whispering in his ear. Although he pretended to not know who it was, he knew all along that it was her. As they spend time together and reminisce about their past, they realize that they still have strong feelings for each other. Despite their history of not working out in the past, the narrator can't help but feel that things may be different this time. The lyrics convey the narrator's admiration for his partner's appearance, as he repeatedly mentions how good she looks in his shirt. This serves as a metaphor for feeling proud and fulfilled to have her back in his life. The song suggests that while it may be too early to determine if their relationship will ultimately succeed, the narrator is willing to explore the possibilities and embrace the happiness he feels in her presence. Overall, "You Look Good In My Shirt" portrays a story of hope, reconnection, and the possibility of a second chance at love.