I can't help but feel that in fact the high tops don't belong in the Unc fit, that very different shoes would change the entire look. Also, the shirt "wash" vs the pant "wash"... that they are so similar, yet different, gives it a very canadian tuxedo, top to bottom, appearance. Like how the denim jacket never entirely matches the denim jeans.
The "I don't care about femininity" excuse regarding the glasses and bag doesn't fly with me because I don't particularly find the rest of the outfit to be over the top feminine. I find those pieces to be feminine and incongruous and bad.