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The Playboy Bunny exists because it is hard to serve an Old Fashioned in a nightgown. In 1960, when Hugh Hefner was launching his first Playboy Club in Chicago, he had a dream: cocktail waitresses in short nighties. This idea was thrown out as entirely impractical. Instead, Ilse Taurins, a Latvian refugee and girlfriend of an investor, had her mother sew a bunny costume with ears and a corset, cut high up the thigh and adorned with a little fluffy tail. Practicality incarnate.

That was more than a half-century ago, but there's nothing retro about the Playboy Bunny suit these days: The iconic image is ubiquitous, breeding like … you know. Fighting back against the free porn that's cut into his profits, 86-year-old Hef is working his brand with a vengeance. There's a new iPad version of the magazine, a new club in London and plans for one in Chicago, bunnies in a Vegas casino and a TV show called The Playboy Club, narrated by Hefner, launching on NBC this month.

The Bunny suit – that Halloween party staple – is still Playboy's logo, but it could also serve as the emblem for our cultural confusion around sex and fashion. One day last month, The New York Times ran a pearl-clutching think piece over the rising hemlines and topless parties of college girls gone wild. Soon after, a 20-something at Slate rolled her eyes in a rebuttal called Smart Girls Wear Short Skirts, Too, embracing the I-own-my-sexuality ethos of the Slutwalks. Such is the chasm that the Playboy Bunny has been hopping around in for years: Is a half-dressed lady empowered or exploited?

Don Draper's horny backward glance has injected mid-century fashions into the mainstream, awakening appetites for a bustier, aggressively feminine silhouette. Mad Men didn't even air a new season this year but its influence was widely felt. The show's costume designer, Janie Bryant, is behind a new line of retro-inspired clothes for Banana Republic. ABC will air Pan Am, a series about sexy sixties stewardesses shaped like hourglasses. And The Wall Street Journal reports that designers like Marc Jacobs, David Koma and Riccardo Tisci of Givenchy have punctuated their fall collections with "Bunny-esque fetishism that includes binding body suits, furry pom-poms and other homages to kink culture."

But the Bunny suit was never overtly about kink. Hefner's brand of sexy was rooted in a girl-next-door fantasy. The original Bunnies were recruited through an advertisement that read: "[A Bunny]may be sexy, but it's a fresh, healthy sexy – not cheap or lewd" (what a healthy girl might do behind closed doors was the engine of the fantasy). Fashions of the time, like wiggle dresses, bullet bras and cinched waists, played on the idea of sex but not sex itself, hiding the female form while accentuating it. For all the sartorial provocation, the club had a no-touch policy, which reflects the Joan Holloway strategy of dressing: Grab the attention, but control the outcome.

Maybe this is why the last line of The Playboy Club pilot, recited by Hefner, is: "Bunnies were some of the only women in the world who could be anything they wanted." Since, in fact, women working at the Playboy Club could only "be" bunnies in interchangeable outfits, this comment must refer to money: One early-sixties Bunny reported making $1,000 in tips per week.

But is financial solvency the only definition of empowerment? In 1963, Gloria Steinem went undercover as a Bunny to expose the ugliness, comic and tragic, that sustained the fantasy. In a magazine piece, she described dry-cleaning bags and Kotex pads stuffed into bustiers and wrapping gauze around her torso to stop the corset's boning from ripping open her skin. The uniform was so painfully tight that a sneeze could break the zipper. Potential hires endured internal exams and weigh-ins, with zero job security.

Needless to say, Steinem is no fan of the new series and called for a boycott last month: "It normalizes prostitution and male dominance ... I just know that, over the years, women have called me and told me horror stories of what they experienced at the Playboy Club and at the Playboy Mansion."

Which takes us right back to the old "choice" argument: If women themselves choose to exploit their sexuality though clothing, as Bunnies or as Snooki, then there's no problem here, move along. But surely some Bunnies would have chosen to be Don Draper rather than serve him cocktails, if that path had been available. One of the great pleasures of Mad Men (which has many female writers) is that it's acutely aware of the limited choices afforded its female characters and doesn't make a virtue out of the fact that sex was one of the few powers in the female arsenal 50 years ago. But it's 2011 – should we not climb out of the rabbit hole?