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I think you look fantastic in the first group of pics, but as others have said, your MIL may not be Rick Owens' intended audience? My sweet MIL would have thought that outfit terribly plain and sad-sack, while my mother (judging by her reaction to my silky track pants) would think you'd lost your mind. And, although it isn't necessary to costume yourself in her taste, you don't want to be a distraction, either. You know the lady best--what does she admire and appreciate on you?