I have a Chanel bag from my grandmother from the thirties, but I keep that wrapped and put away and only use it for very special occasions.
I have a pair of Sebago Docksiders I bought in 8th grade (we're talking 1981 here). I saved money from my summer job to buy them; they were the unheard-of price of $39.99! lol They're pretty ragged but I still wear them