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So basically, assuming I interpreted that correctly, even if Oresky's example wasn't a ZCE, Tropes Are Flexible can only go so far, and in this case it doesn't go far enough for him to be an example, right?
Edited by ryanasaurus0077^ Yeah. Tropes Are Flexible, but Not That Flexible. Hats!=Glasses by any stretch of imagination. The most flexible I think it could be would be to define "glasses" in the context of the trope as an accessory that clearly marks the character as a nerd, or an intellectual, or otherwise not a physical combat type. Like, I don't know, a pocket protector or a retainer. And even then you'd be really stretching it.
That is one major problem with appearance tropes; they confuse the appearance with the characterization that it is intended to invoke. Pocket protectors, thick glasses, and such are an example of stereotypical nerd accessories. That's the trope, not "thick glasses".
The Glasses Come Off is not about the item of apparel; it's about a transition of the character from introverted to extroverted, meek to badass, dorky to sexy — symbolized by the removal of a stereotypical 'nerd' accessory. I can't imagine anything about a hat that evokes similar imagery.
"It's Occam's Shuriken! If the answer is elusive, never rule out ninjas!"

Are glasses and hats synonymous with each other, or is Oresky Not An Example of The Glasses Come Off? I've removed it from the character sheet until further notice and will readd it if it is indeed an example. If Tropes Are Flexible doesn't apply here, then I don't know what else could possibly justify someone who doesn't wear glasses being an example of that trope. If Tropes Are Flexible doesn't apply here.