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OP, I'm wondering if there's something you wear that reminds him of his mother, who is probably in her 50's. I could see how that might trigger a comment.
I love comfy clothes too but usually I'm in sundresses or shorts and cute tops. I wouldn't consider a sports bra comfy or cute.
My husband keeps mentioning the halter tops that I wore in high school. I may surprise him some night. And we're old, in our 60's, but still fun.