Josh and Bret dig into a big question: What does it even mean to be cool anymore? Is it still a leather jacket and cool-dude attitude… or is it now a curated Instagram aesthetic and hipster energy?

We’re talking about how Gen X defined cool--think Starter Jackets, Grunge Dr Marten, Track Suits (were they ever cool), and not trying too hard, and how the definition has totally shifted. Is “cool” now just algorithm-approved relatability? Do dads get to be cool—or are we just here to embarrass our kids in cargo shorts?

And most importantly—have we finally aged out of cool, or is Gen X quietly still holding the crown because we just don’t care?

And for the record, neither Josh nor Bret wear cargo shorts thanks to our wives who keep us dressed appropriately.