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Every time my wife worries about not wearing the same thing, I get her to list any outfit the others were wearing last time.
It's all in your head.
I've worn the same dress to pretty much every holiday and family event for at least the past 8 years. I don't know if anyone thinks it's weird or wrong. What I do know is that every person I've dated within that timeframe has told me that it's their favorite of my outfits.
And that's the closest I get to caring what anyone else thinks about it.
My wife had people asking if she was going to wear her awesome sequin dress to her Xmas party one year and were sad she was going to try something else, all of them older (40s-60s)
She and I both have only ever heard of this whole "don't wear something to 2 events", my mom (late 50s) has also never actually seen it in person. Maybe we're too poor?
I can’t recall things like this if I just think about it, but if I see it again I instantly recall.
But I definitely do not care if someone wears the same outfit repeatedly