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For me, I find most pretentious- overly academic names, fussy British names, feminine names used on boys, flowery names or very extravagant names, or titles. I also find many of the hipster / ultra trendy 'cool' names to be incredibly pretentious.

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Boys
Prescott
Alistair
Ambrose
Aubrey (Male)
Basil (especially pronounced Baz-ul)
Hilary (boy or girl)
Magnus
Sebastian
Cassius
Eustace

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Girls
Cordelia
Ariadne
Bridget (maybe it's just me, I've never known a Bridget who wasn't pretenious
Hilary
Guinevere
Beatrice
Eugenie
Anastasia
Bella names like Arabella, Clarabella, Isabella, Orabella
Persephone (or any Greek mythology name especially if it ends in -phony)