As a youth dressing as Caspar the Friendly Ghost three years in a row until the costume could no longer fit.
At about 8 or 9 not being able to trick or treat because my parents were scared we’d get kidnapped or poisoned.
Side note: Underoos came out the year after I was too big to fit in them. This caused a melancholy that lasted for years.
At 18 dressed up for a Halloween party with adults and feeling ridiculous in a costume. I remember exactly what I wore and am still too embarrassed to admit it.
At 24 thinking I’d come up with a cool at-that-time obscure pop culture character to
dress as and then getting progressively more depressed as one, two, then three other Zorros, each one more accurately and expensively attired, the final one with an actual sword, walked into the party.
All through my 30s my costume was that of a hard-working professional. What I was underneath that, who knew?
At 40 attending a costume party as Satan in Pennsylvania and progressively losing my horns, my tail, and my bowtie by the end of the night.