Issue him a #latepass on trends he once hated but has since adopted.
How to do it: "Oh cool man, I see you've discovered Air Force 1s."
Some guys' style never stops evolving. Shout out to Four Pins' Lawrence Schlossman, who once swore never to wear sweatpants and rocked a shit-ton of tailored menswear, but now is always spotted in some form of denim and sneakers. There's nothing wrong with that, but it doesn't mean you can't give them shit for it.