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ChristianKl comments on Stupid Questions April 2015 - Less Wrong Discussion
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The path I see is to develop more specific preferences and articulate why you prefer certain clothing over other clothing. Tell your relatives what kind of clothing you like.
You can even say: "I have make a decision to move to a new style ..." If you don't want to make them feel bad for past gifts.
Clothes I pick often depend on my mood and the social context I will have in the day. If the emotional state in which you buy radically differs from the state in which you choose clothes from your wardrobe that can lead to a disconnect.
Have you analysed why you prefer certain clothing over other clothing?
Thank you, I'll try. I prefer warm to pretty in winter and khaki/colourful (depending on whether I am with my kid or not) to neat. I prefer pants to skirts. Generally, I like only a narrow subset of how I can look, and get annoyed when people tell me to be more flexible. My thinking goes like 'can't they see I have already defined myself and have no wish to follow aging conventions?' (I'm 29.) It's a bug and not a feature, but I find other people's clothing so... hopeless, I guess, so muted, that I can't remember the last timeI envied someone.
If that's true it's likely that it you could be more specific then pants>skirts and khaki/colorful.
On the other hand those seems pretty straightforward rules for your relatives. Don't gift her skirts and make sure it's either khaki or colorful.