I first did it around 1970, in Boston. My mother knew about it and was mortified.
My grandmother found out and nearly fainted. Fortunately, my father was
oblivious. Every once in a while I still do it, just for fun. I still get psyched every once in a while, before a big party or a wedding.
My first time was in Kenmore Square, in a funky loft upstairs where with a little
babysitting cash I could pretend I was in Haight-Ashbury or the Village,
not eighth grade. I was hooked.
That first purchase was a pair of Levi’s, Big E 501’s to anyone who appreciates that, so mellow and broken in they felt like suede. 
Then came a gorgeous velvet riding jacket. A pinstriped men’s vest with a satin back. Old boys’ pique tuxedo shirts. Flannel cowboy shirts with snaps. Big chunky leather peep-toe shoes from the 1940s. A vintage kimono and a Bakelite/rhinestone bracelet. An alligator clutch. A fur stole complete with beady little eyes and teeth. Thirteen-button sailor pants — navy melton — surplus from the army-navy store. Every few winters a new peacoat. I could not wear an army jacket; Vietnam was still nightly news and those felt a little too real. The only sailor I knew of was Popeye, so the pants I could easily romanticize. My mother gagged. “How can you wear someone else’s clothes?” “How do you know where it’s been?” my grandmother chimed in regularly. “They could have crabs.” They didn’t, and I didn’t, and I never heard of anyone contracting crabs that way.
While we’ve been paying attention to things like mortgages and tuition, vintage has
crept up to become late 1970s and early ’80s. Leg warmers. White scrunchies. Day-Glo pink hi-tops. Slouch socks. Wide, wide belts. Tapered jeans. With little zippers
at the ankles. So if you are now past mid-century modern on the age
census, don’t get rid of anything in your attic too hastily. A recent NY Times full-
page ad showed the new & “edgy” Gap jeans. With little zippers at the ankles.
That first pair of Levi’s in Kenmore Square? Starting bid is $375.00 on eBay.