Here are the coordinates I would set:
Date: July 28, 1960.
Place: Madison Avenue, New York, New York.
Here is what I would pack:
A gray suit, a white shirt, Jousting Knight cuff links, a skinny tie, black frame glasses, and I'd walk the avenues uptown, hatless, as was the trend with the stylish young men that year.
And a married man traveling back in time can still let a broad in a sudden red dress catch his eye, can't he? Probably not. That would maybe be a little too fresh. I love my wife so much, I'd experience irrational guilt. I'd then have to set up thrice weekly sits on a psychoanalyst's couch.
Barring time travel, I guess I'll just have to wait for season two.
Mad Men, in case you don't know, is the AMC series about one of the cogs that moved the wheels of post-war consumer culture, the Advertisers who worked on Madison Avenue, New York. The highly-stylized show, set in the summer and fall of 1960, is more than an exercise in period dress, design and diction. The show focuses on the dynamics of an ad agency in that period of American history just after men stopped wearing hats and just prior to when women, at least the daring ones, began wearing pants. Yet socio-political attitudes are still very much those of the previous decades. Everyone smokes and smokes, everywhere, drinks like fish, and eats like razorbacks. The show does a fine job of not romanticizing these excesses while still showing how individuals fell under the sway of being an upper middle class New Yorker in 1960.
It has the surface texture of good post-war suburban/urban malaise fiction such as Richard Yates and John Cheever, while attaining the psycho-cinematic moxie that the Slavoj Zizek crowd enjoys so much. You really need to check out this show if you haven't already. I mean, look at these characters:


You can watch the whole first season here.