I think it depends. Some people don't really bother with what they wear in dreams and don't pay attention; among those who do, some probably wear headgear in dreams and some don't. For instance, I normally wear glasses, but I have perfect sight in dreams even though I don't feel the glasses.
The same applies to WILD, I believe. If you fall asleep while paying attention to your headgear, it will probably remain in a dream; if you don't, it probably won't until you question yourself why.




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