Yeah, especially the first part where he has to undress first...
But his shirts, they all must have some sort of "sleeves" or holes for his wings. I was thinking of how he could push his large wings through such holes, against the direction of the feathers, and it made me realize that no, he wouldn't do that, it has to be some other solution. So I came up with the idea of the buttons. He'd simply wear his shirt under the wings, and then pull it up and button on top of them. Or another solution can be a huge hole for both wings and fire.