Thinking like this will probably land you a one-way ticket to hell (so what else is new?), but consider the grandparents as your one-stop shop for cool, of-the-moment accessories. Hit up Mamaw for her cameos and little top-handle bags. Then, after she's handed them over—along with a $10 bill and a pat on the head—accost G-Pa. As Wiz put it, "How could we not talk about family when family's all that we got?"
He might seem an unlikely source, but ton grandpère has a few sartorial assets up his sleeve, specifically his glasses, which have become a social media sensation amongst the young and stylish set. (Props again to Gucci, starter of eyewear trends left and right.)
But some advice before you go nicking any bifocals: As always, the path to success is to treat it as if you had no idea how it happened the first time so as not to cloud your judgment. That is to say no cardigans, no day-off sweats (too sloppy), and nothing too '70s (though that can be very chic if your aesthetic already leans that way). And, if none of the below appeal to you, make sure you're taking Pop-Pop's spares—he still needs to see, after all.