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Traveling was one of the best things that ever happened to my mother. It made her feel more confident, as if she finally had something in common with her own mother. She still didn't remember a lot of details about her, though after she spotted the gold shoe around my neck, she remembered that I'd taken it and wanted it back.

“It was given to her by her first love,” she said.

“Was he the man she ripped out of the albums?” I asked.

“Yes. His name was Jack.”

“Jack the Ripper?”

“Patricia, that's a horrible thing to say about your grandmother. I can assure you that she didn't date Jack the Ripper.”

“Yeah, because she'd have been dead.”

“Can I please have my gold charm back?”

Naturally, I gave it to her. She'd earned her traveling shoes.

In the Heights

W
hen I moved to the Upper West Side in 1976, I received a lot of unwanted attention from a drug addict who lived in Verdi Square, across from the 72nd Street subway station. Named after the Italian composer Giuseppe Verdi, it was more famous as Needle Park, a popular destination for drug users and dealers, as well as the setting for
The Panic in Needle Park,
starring a very young Al Pacino. Except for the needle dangling from his arm, my drug addict looked nothing like Pacino, though he did have the actor's talent for over-the-top line readings. Despite his addled condition, he still managed to summon his full vocal power to comment on my appearance as I raced to the subway each morning. “Your ass looks
waaaay
too big in those pants,” he'd yell. “Or no
waaaay
is red your color.”

Before long, I was factoring his slurred comments into my daily wardrobe routine. This was absurd for many reasons, not the least of which was the man's own style, which relied heavily on cardboard, plaid rags, and a floral nightgown fashioned into a kilt. Once he called me over to where he was lying in a pool of his own urine to inquire if he could ask a “personal question.” Since his good manners offset his vile odor, I agreed. Pointing to my brown suede loafers, he said, “You're never gonna get a man in those things! They're
waaaay
too ugly!”

Since this happened right after I'd split up with Scott, I was feeling particularly vulnerable. Were my loafers a turnoff to men? As I waited for the subway, I wondered why was I taking fashion advice from a homeless drug addict. Was I that insecure?

The answer, I'm sorry to say, is yes. Which brings me to my love/hate relationship with high heels. I love the way they look but hate the way they feel. I wish it were otherwise. I wish I could run, skip, and jump in five-inch platforms, but I can't. I'm convinced few women can, only they fake it better. Or maybe it means more to them than it does to me, but since I'm writing this book, you've got to figure it means quite a bit.

My limit is two inches, maybe three, but even that turns me into the martyred Crispin and Crispinian, the patron saints of shoemakers. Crispin and Crispinian were possibly brothers, maybe even twins, or most probably fiction. (During Vatican II, they were “delisted” as saints.) Crispin, whose feast day falls on October 25, is the more famous brother, thanks to Shakespeare's
Henry V
and its inspiring St. Crispin's Day speech. Henry, heavily outnumbered, rouses his troops to fight the French at Agincourt, uttering the celebrated lines “We few, we happy few, we band of brothers.”

Depending on the source, Crispin and Crispinian were French or part Italian and British. They made shoes at night and preached Christianity during the day, which prompted the Romans to devise various tortures to force them to recant their faith, including drowning, burning, and placing them on the rack. If the brothers had lived in the 1990s, the Romans could have placed them in Vivienne Westwood's nine-inch platforms—the very shoes that caused supermodel Naomi Campbell's infamous catwalk tumble—and forced them to sprint up and down the Spanish Steps.

For most of my life, I avoided the high-heel dilemma. I was too young for the stiletto craze of the 1950s; I embraced the flat styles of the sixties; I ignored the platforms of the seventies; and during the eighties, I wore low-heeled pumps with my broad-shouldered “power suits,” which in retrospect were ridiculous and made me look like Joan Crawford. Still, I could walk. And then, in the early nineties, grunge came along and ruined everything for me.

The style emerged from the scrappy garage band scene in Seattle, where it was linked to Nirvana frontman Kurt Cobain, who mixed lumberjack clothes with feminine floral prints. Cobain, a heroin addict, later committed suicide but not before marrying Courtney Love, who was also addicted to heroin and who popularized the “kinderwhore” look—torn Baby Doll dresses, cigarette-burned stockings, smudged makeup, and Mary Janes or military boots. For his spring 1993 collection, Marc Jacobs, who was then creative director of Perry Ellis, sent Christy Turlington, Kate Moss, and former first lady of France, Carla Bruni-Sarkozy, down the runway in fashion's version of grunge. The models wore plaid-printed “lumberjack” silks, thermal cashmere sweaters, crocheted beanies, and chunky Doc Martens, which had been a symbol of urban rebellion long before Nirvana. Skinheads wore them. Punks wore them. Malcolm McDowell and his fellow droogs wore them in
A
Clockwork Orange.
Elton John wore a giant pair as the Pinball Wizard in the Who's
Tommy.
I'd have worn them too because they looked comfortable, but grunge wasn't for me.

It also wasn't for the executives at Perry Ellis who promptly fired Jacobs. Why did women need to spend a lot of money on Salvation Army–inspired clothes when they could go directly to the Salvation Army? In retrospect, my drug addict, with his fondness for floral and plaid, was into grunge long before it even had a name. He may well have invented it.

As a reaction to grunge's androgyny and lack of sales appeal, a new trend emerged, one drawn from “Girl Power,” which was a rebuke to 1970s feminism, or, as writer Naomi Wolf labeled it, victim feminism. The “postfeminist” woman could be girlish and powerful. She could present herself as a sex object because she was “owning” it, along with something else: shoes. The stiletto was the weapon of choice for the new power-seeking, sexually assertive female. Though many designers adopted the trend, Tom Ford received the most attention for his modern interpretation of 1970s decadent glamour. Integral to the look were extreme shoes, such as metal-heeled stilettos with bondage leg ties. Collaborating with photographer Mario Testino and stylist/muse Carine Roitfeld, the designer helped create an eye-catching ad campaign that promoted his “porno chic” aesthetic. Though not as perversely shocking as Guy Bourdin's 1970s photos for shoemaker Charles Jourdan—one showed the outline of a body on a blood-splattered pavement—they presented the merchandise in a violent, sexually charged way.

Anyone who has ever worn high heels or watched anybody walk in them knows how they emphasize a woman's anatomy, pushing out her breasts, elevating her butt, and making her hips swivel. According to the scientific journal
Evolution and Human Behavior,
it's the reason men prefer women in heels. The authors go on to compare these women to “female baboons with a larger than normal swelling of the bottom associated with the sexually receptive period of their cycle.” This led me to google
ovulating baboon
, and I wish I hadn't. A picture showed the baboon's bottom not only greatly engorged but bright red. In 2008, social psychologists at the University of Rochester conducted a study that concluded that men found women dressed in red more attractive than ones wearing chromatic colors like green and blue. In their sexual response to women, they are not far removed from baboons. They like big bottoms and they like red.

Female activist Beatrice Faust believes that high heels are not just a turn-on for men. By making the buttocks undulate twice as much, they spread sexual sensations throughout a woman's body. Since I've never walked far enough in high heels to experience multiple undulations, I'll have to take her word for it.

My plan was to ride out the stiletto craze until fashion reversed itself, but the popularity of
Sex and the City
made that impossible. The show was a paean to shoes, turning Manolo Blahnik and Jimmy Choo into superstars. Designer high heels had never been so highly coveted, which made my World Is Flat theory seem totally archaic.

Finally, I broke down and bought a pair of three-inch Manolo Blahnik Carolyne slingback pumps. They were created in the 1980s for the former fashion designer Carolyne Roehm, who was then married to billionaire financier Henry Kravis and lived in an opulent Park Avenue duplex. That is not the reason I bought the shoes. I bought them because they were classic. “I'll have them forever,” I told Lee, who said, “No, you won't, because you won't be able to walk in them.” If Carolyne Roehm could walk in them, I could. Of course, Roehm had a car and driver, but at some point even Carolyne had to walk in her Carolynes.

For centuries, shoes have been a mark of wealth and status, high heels elevating aristocrats far above the crowd. When the heel was first invented in the sixteenth century, it wasn't economically feasible for cobblers to make “paired” lasts for right and left. Instead of giving up their heels, people preferred to wear “straight” shoes that over time conformed to their feet. In France during the eighteenth century, Louis XIV made the red heel—the
talon rouge
—a symbol of nobility; only members of his court were allowed to wear them, as long as they were lower than the king's. With its concave curve and outward taper at the base, the Louis heel became very popular with women, until the French Revolution put an end to any outward sign of ostentation, and flats returned to fashion.

With this in mind, I approached my Carolynes from the perspective of someone lucky enough to live in an era when I didn't have to sacrifice left for right or worry about losing my head. Marie Antoinette would have loved Blahnik, which is probably why Sofia Coppola chose him to design the shoes for her movie about the French queen. His styles tend to run small and narrow, with a pointy toe box. This lends the illusion of small, dainty feet, which men are said to prefer, even though some of the world's sexiest women, such as Angelina Jolie, Uma Thurman, Heidi Klum, and Charlize Theron, wear size 9 and larger. In China, the tiny foot was so highly prized that it led to the practice of foot binding, which involved breaking all the toes, except the big one, and then continually wrapping tight cloth around the foot. The result was the aesthetically pleasing “lotus” shape, which like genital mutilation was thought essential for a good marriage. When foot binding went out of fashion in the nineteenth century, many husbands abandoned their wives for the same reason they'd married them.

My first outing in my new Carolynes took place at Lincoln Center, where the film society was paying tribute to the star of
The Panic in Needle Park
—Al Pacino, who, coincidentally, once worked as a shoe salesman. After the tribute, there was a dinner at Tavern on the Green, which involved walking from Avery Fisher Hall across Broadway and Columbus, down West 65th Street, across Central Park West, and into the park. I know you're supposed to “break in” new shoes before wearing them, but whenever I hear that phrase, I think of the scene in
The Misfits
when Clark Gable breaks the wild mustang so he can sell it to a dog food manufacturer. Marilyn Monroe is so poignant as she tries to stop him that I've long since forgiven her for helping to make high heels a standard for feminine beauty.

By the time I reached Broadway and West 65th Street, I realized that my Carolynes were breaking me. “You go ahead,” I called to Woody and Warren and their wives. (Warren was now married to a vivacious former CEO and they would soon have two children.)

“I thought you said they were comfortable,” Lee reminded me. “You said they were classics.”

“They are classics, but classic is different than comfortable, and my toes are getting squished.”

We stopped in the middle of the block, where I pulled off my right shoe in front of a mountain of black garbage bags. As I balanced on one foot, I felt something scurry across my left shoe. I looked down. It was a huge rat. If Lee hadn't grabbed my elbow, I'd have fallen headfirst into the mound of garbage. I tried to imagine the rat as a benevolent Disney rodent, like the sweet mice that helped Cinderella redesign her ball gown, but it was too disgusting. I managed to reach Tavern on the Green but couldn't forget the sensation of the rat's tail brushing against my ankle. From then on, my Carolynes no longer evoked the image of an ex–fashion designer and society hostess, but one of those inflatable rats with gigantic teeth and scabby bellies that unions place in front of buildings to protest employment practices. No heel had ever come down to earth so quickly. When Lee began referring to them as Carolyne the Rat Shoes, I knew that Carolyne and I had to split up. They were my trophy heels, and while I couldn't offer them a hefty settlement, I could give them a nice funeral, shrouding them in their white shoe bag before placing them in their Blahnik boxed coffin. They're now safely interred on the top shelf of my closest, next to my Lucchese Western boots, which I haven't worn since 1979, and probably never will.