The poem's similes capture the speaker's sense of insincerity while also warning of such insincerity's dangers. "Once upon a time," the speaker tells their child, they used to be a warm, open person living in an equally warm and open society. Things have changed now, though, and they have had to learn "to wear many faces / like dresses" in order to get by. In this simile, the speaker's outward presentation becomes a costume; they put on expressions like outfits, changing "officeface" for "streetface" and "homeface" for "cocktailface" as necessary. The look their face wears, in other words, has nothing to do with how they're actually feeling.
This simile also implies that there's a different, more honest, naked feeling beneath all those fancy metaphorical clothes. In a society that runs on concealment, the speaker feels that they, too, have to cover up. They also have to make sure that this cover-up looks good. The "conforming smiles" that the speaker wears out in the world are "like a fixed portrait smile": a fake, slightly strained beam like the one you'd see in a posed photo. That simile suggests the speaker is anxious to make a good impression. Just as a photo portrait is meant to capture a person at their best (and often ends up capturing something rather artificial instead), the speaker's smile is meant to suggest they're perfectly at ease with the way things are. Clearly, that's not true.
All this pretense means the speaker ends up feeling false on the inside as well as the outside. When they look at their own "laugh in the mirror" these days, they see no real joy: just their "teeth like a snake's bare fangs." That dangerous image hints that a life of deceit can become downright poisonous. It also draws on traditional snake symbolism, in which the snake is often used as an image of trickiness and dangerous deceit. The speaker, to their horror, has become as much of a snake in the grass as any of the other people they despair over.
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