The last couple of days I broke out a 70's acrylic golf cardigan I've hardly ever worn, despite owning for a decade. Its a strange yellowy-green color, something you'd only see in the 70s, and I've always been a bit doubtful about it. I'm also wearing a vibrant medium blue hospital orderly's polo with the hospital insignia on the breast, and dark brown trousers, with a cloth belt and black low-top converse, sockless.
And I actually got a compliment from a Thai girl at a hip coffeeshop on my weird sweater!
I find that trotting out pieces of clothing from decades ago can indeed generate compliments from those too young to see the clothes as old and tired.