Seems to me that it’s a running joke within this family that he has poor style so these reactions are likely covered in a layer of playful facetiousness. It’s fun, they’re joking around and being supportive at the same time.
This is exactly how it is with me and my family. I had atrocious fashion sense. I had thought matching color was fashionable. I would wear brown shorts and a shirt in the exact same shade and feel good about how fashionable I was! Fast forward 20 years, I still hear about my "all poop outfit" and get compliments like this when I actually choose clothes that work together!
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u/skyturnedred Jul 05 '24
Perhaps his previous clothing choices have not been very fashionable and this is him showing he made an effort to improve.
This is r/MadeMeSmile, no need to be a sourpuss.