I don’t know, those look like girl boots.
Puerto-rican fence climbers
Yep, they look faggy to me. Too GQ. If he wants to wear boots, he would be better with some good American-made cowboy boots. But my advice is for him to simply get something like Allen Edmonds black dress shoes and call it a day. He shouldn’t try to be something he’s not. If those boots are who he is, well...
Yeah, very feminine, and maybe its his pants are too short.