It’s interesting to note when Tony takes his sunglasses off and when he wears them. The lack of sunglasses usually depicts his vulnerability and sincerity, whereas its presence signifies that his game face is on.
Hence, when he has a heart-to-heart with Rhodey and when he is trying to encourage Peter to formally be an avenger, he takes off his sunglasses. In CA:CW, as Tony is discussing the Accords with Steve, he doesn’t wear sunglasses. However, when his entreaties are dismissed and the negotiations fall off, we get a scene of Tony putting his sunglasses (his game face) on as Steve walks away.
There is almost no scene in which Tony is wearing his sunglasses when talking to Pepper. He is always ‘bare’ when talking to her, even before Afghanistan. The one time we see him wear any eyewear while talking to Pepper is in IM3 (a movie in which Pepper is visibly upset with how Tony uses tech to hide his mental health issues). In this scene, what Tony is wearing is not his usual sunglasses, rather some sort of techie-glasses; and he wears it while he is having an argument with Pepper regarding his mental health, his “tinkering”, and his obsession with his suits as a coping mechanism. As the argument winds down with Tony confessing his fear, insomnia, and anxiety to Pepper, Pepper walks to him and gently removes his ‘techie-glasses’ and leaves him bare... And he looks up to her in gratitude for it.
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