Additionally, he’s making reference to the coolness he will have recognized by “sneaker heads” or athletic shoe enthusiasts by ironically wearing used, yet already cheap Payless shoes.
He may also be sticking with the senior citizen dress theme, as older people often wear velcro shoes due to their fine motor skills (used to tie laces) escaping them in their old age.
Also, Pro Wings were like a mark of shame in middle school. They reflected poverty or cheapness and people who wore them were teased relentlessly. They looked like space shoes — he even mentions them here in his song Wings, saying you would get clowned on for wearing them. It’s ironic now that Macklemore could take such a stigmatised brand of shoes and make them desirable to the sneaker nerds.
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