Dude...Where'd You Get That Sarong? Jon-Jon Goulian's 'Man in the Gray Flannel Skirt'

Is there anybody more likable than Jon-Jon Goulian? Toned, tanned, bedaubed with fantastic eye makeup—the first and only cross-dresser ever to have worked at The New York Review of Books—Mr. Goulian has made friendliness his life's work, tricking successive generations of newcomers into thinking that the New York literary world is populated with attractive and unusual people.

When word dropped in 2008 that Mr. Goulian was writing a memoir, and that he had received a $700,000 advance, the publishing industry rejoiced. For years, the city had been using Mr. Goulian's elegant sarongs and indeterminate sexuality as a salve against drabness; a book deal meant he was at last earning recognition for his atmospheric contributions.

Now we know that Mr. Goulian's bonhomie has been hard-won. Likability, and its nervous analogue, the desperate need for approval, are the structuring themes of The Man in the Gray Flannel Skirt (Random House, 336 pages, $25) a "making-of" memoir that traces the emergence of a tattooed, glam boy layabout from a Jewish-American childhood spent among eminence-driven achievers.

Mr. Goulian's mother is a successful lawyer who works long hours; his father is a well-known hematologist and health food fanatic; his two older brothers, unnamed, are scholar-athletes accepted to Harvard and Yale; his grandfather was the late political philosopher Sidney Hook. Growing up alongside so many winners leaves little space for Jon-Jon to distinguish himself. To make matters worse, the family lives in La Jolla, Calif.—a "theme park on the beach"—burdening the praise-addicted Mr. Goulian with a range of beauty-related pressures unknown to a Gopnik or a Foer.

As a young boy, Mr. Goulian has it relatively easy—he's a good-looking soccer star with plans to become a surgeon. Things head south after his middle brother goes off to college, abandoning Mr. Goulian to "the overwhelming love and scrutiny of my parents." His body begins to betray him: his nose swells, his legs start to bow and, most worrisome, he grows what seems to be a third, undescended testicle (it turns out to be a stray pies of intestine). The triple threat saps Mr. Goulian of inner strength, spurring a lifelong dysmorphic quest to conceal and correct bodily imperfections.

Mistakes are made along the way. He ruins his gums through overzealous flossing. He parches his skin with astringents. At 15, he asks his mother for a nose job, and she agrees, satisfying him for nine years until he decides he needs another. He smiles with his mouth closed, pivots his body to block the "weak" side of his face, and walks in "frenetic diagonal movements" to avoid exposing his bowlegs. 

The decisive event of Mr. Goulian's early life is the moment he learns he's scored a 650 on the Achievement Test in Math (the easy one). He erupts in tears, scrawling in his journal "I can't handle this intense life. ... Maybe I'll just drop out of school and marry someone wealthy." After examination Armageddon, the dominoes fall. He quits soccer. He starts wearing lip gloss and Ugg boots. He fails to enroll for Advanced Chemistry. He goes to prom wearing white tights, black pumps, a black skirt, red lipstick and a red bow tie.

The next year, when he enters Columbia—not generally considered a second-tier school, but not the Harvard or Yale of his older siblings, and in any case Mr. Goulian points out it had a worse reputation in that era—he is heckled as a "faggot," a "freak" and, this being the '80s, an "AIDSmobile." He takes refuge at Barnard, electing to live in a women's college rather than risk hostile encounters with the football team. When he tries to get a summer job manning the cash register at Chic Accessories, a jewelry store in a San Diego mall, he's fired on the first day for arriving in yellow overalls embossed with "riotous," honey-swilling bumble bees. After graduating, he enters law school, but rules out becoming a lawyer on account of the dress code: wearing a tie with a collared shirt makes your head appear smaller, and Mr. Goulian's head is on the small side to begin with. In need of a job where no one will notice or care about his sartorial peculiarities, Mr. Goulian eventually finds work at The New York Review of Books.

Sex is another source of trouble. His encounters are few, and each is more or less coerced. Girls named Zoe, Edie, Daphne and Stevie are among the assailants, as are boys named Oliver and Gunnar. (Mr. Goulian admits that some names have been changed to protect the innocent.) "After my encounter with Zoe," Mr. Goulian writes, referring to a 14-year-old stranger who gives him a blow job and unsuccessfully tries to coax him into coitus in bushes next to a mall parking lot, "my sexual curiosity waned considerably." An experience with a girl at Columbia during freshman year leaves him so traumatized he has trouble getting out of bed for days. The "mammalian tendencies" of the female body disgust him, and erect penises cause him to "flee." His one object of sustained (unrequited) lust is a genderless anorexic girl referred to as "the Vegetable Monster." In an ill-conceived attempt to get her attention, Mr. Goulian drifts into anorexia himself. It's only later that he turns to bodybuilding, an interest he explains as an effort to direct attention away from his face, which he cannot change, and to his arms and stomach, which he can push toward perfection.

Mr. Goulian's sexuality remains a puzzle even to himself; no amount of gender theory, with its formidable array of terms—"bisexual, transsexual, polysexual, metrosexual, metasexual, autosexual, cryptosexual, crypticsexual, protosexual, extraterrasexual"—provides an adequate explanation. Mr. Goulian himself settles for a lengthier qualifier: He is simply the Man in the Gray Flannel Skirt.