TM+wing+tipped+shoes

@http://www.thefreedictionary.com/wingtip+shoe knowing what a wing tipped shoe is completes the theme of the sky. Because if your going to walk on air, it should be with wing tipped shoes. Knowing that wing tipped shoes are real and not something that the poet just made up, also lets you just appretiate and enjoy the poem all the more.

I think the wing tipped shoes are a reference to choosing to be happier, more positive about life. The person wearing the wing tipped shoes is floating, seemingly above the misery. The person in the first stanza has chosen to be sad, as you said, and maybe deserves the misery?