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There's a place in Bisbee, Arizona called the Shady Dell Motel, where you can spend the night in a restored Airstream trailer, listen to Dean Martin LPs, and have breakfast the next morning at an aluminum-sided lunch counter (Dot's Diner). Staying there overnight, I imagine that I'm at a piney campground beside a lake in Wisconsin, flipping burgers in an unbuttoned bowling shirt over a wifebeater with a flattop can of Bud in my other hand.
It's easier to picture yourself in the past than in the present—we know what the past looks like. For now, we take plenty of pictures for posterity—for yearbooks and facebook albums—and trust context to fall into place eventually (knowing that later, too, we can edit out all the nights we stayed in, and never changed out of a t-shirt).
People who "watch Mad Men for the clothes" have it exactly right.