Warbler said:

Gaffer Tape said: But I can't for the life of me figure out how the bottom one looks at all silly or even feminine in the slightest

he is wearing a dress.

Actually, he's wearing a skirt. Or quite possibly a "Utilikilt" or one of the several other brands of skirts marketed towards and created for men, quite like those pantsuit pictures of women you posted. It's completely analogous. He's a man wearing "man" clothes, so there has to be something beyond "he is wearing this" that makes it look silly to you.