Not really as a kid, although I was pretty much the oldest anyway. I had a couple of older half-siblings, but by the time I was big enough for their old stuff the fashions had changed dramatically.
I got given a lot of re-issued kit in the Army and I since bought a fair bit of surplus kit, but that's the closest I've gotten.
On a different angle, I once knew a woman whose wardrobe mostly comprised things her son handed off... He was a pro level skateboarder and got given a metric ****-ton of gear from sponsors, which he wore for as long as his contract required, then gave it all to his mum. She was the coolest, trendiest granny on the streets of Harrow!!