Hand-me-down love

The other day Truman and Shaylie's friend Ayden passed along a couple shirts and a pair of jeans to Truman (technically it was his mom, but you know, whatever).
These outfits became like GOLD to Truman. Nevermind that it wasn't really long-sleeve weather. He has lived in them. He loves them and calls them his Ayden clothes.
It makes me wonder.
At what age do hand-me-downs get their "uncool" reputation?
I'm thinking that once I purchase Truman's outfit for our Jessee family pictures in a couple of weeks, that I should give them to Aydens mom to give to Truman ... because something about wearing "Aydens clothes" makes him smile for the camera all of a sudden!