What not to Wear

Scott and I were headed out to some friends house tonight and this is the outfit he thought he was going to wear. He walked out wearing his dress slacks, nice shoes, leather belt and a mesh athletic top (yes, those are bright big orange "T"'s all over it) and on top of that, he had it all tucked in so nice to show off that dressy belt and pants! He couldn't see anything wrong with this! I am posting these pictures to get your opinion - let me know what you think....is he hopeless or was I just too hard on him??? Keep in mind, these pictures do not this outfit justice!
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Donnie has been known to put together such outfits, too. His favorite used to be his Bjorn sandals with socks... And, he wasn't even 35 doing that! I'm doomed when he is officially an old man. I see black socks and shorts in his future...