Go Vintage, Go.
I really enjoy shopping vintage and used clothes. Many times I can find wonderful deals on outfits that have never even been worn. As a kid I was touted to Goodwill stores on shopping trips, it worked well for me, who always ruined my clothes, and my parents who saved money. I see nothing wrong with it. It's a very good form of recycling and many times, adding to the local economy.
As far as gift giving, I'm not to sure. Perhaps if I found something particular to the person, but in general I agree that it might be misunderstood.