New! – Shoes of the Chicagoboyz

incredible beauty

Dead Sexy: A prominent Chicagoboy shows some foot at a society function.

(A previous Chicagoboyz fashion update is here.)

10 thoughts on “New! – Shoes of the Chicagoboyz”

  1. Looks like the same pair I wore in college. But the scuff by the big toe had grown to a real hole by the time they went in the dumpster. I’d say you’ve got a good 2 years left for that one, more if you wear galoshes.

  2. I have a 2 pairs of old Florsheim Kenmoors (from back when they were made in the US, in black and brown) that are about 20 years old. It’s amazing how long they last when you put a Topy on the bottom, only wear them one day and then rotate to the other, and give them a nice polish with some shoe cream every couple of weeks.

  3. White sox at a function? You wouldn’t be NFL super flopper Gino Torretta, would you? He showed up to the Heisman ceremony wearing a black suit with white sox. You can polish those wingtips up too.

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