In Washington, D.C., there is an excruciatingly narrow margin for acceptable female dress; all women, no matter how attractive or plain, no matter how many postgraduate degrees they have, or how well they fly fighter planes, walk an inescapable fashion tightrope. Their style will fall into the binary categories of either “dowdy” or “slutty”; there are virtually no fashion grey areas.

The default answer to this no-win fashion conundrum, for an alarming amount of working women, is to buy their wardrobes at Ann Taylor; a label so ubiquitous in D.C. it might as well be tattooed on the C7 vertebrae of every woman under 60. The line has always offered tasteful middle-management office classics in wool with just enough spandex to vaguely suggest a Sarah Palin strip-o-gram. My shorthand for the look was always “capitalist burqa” or “corporate office submissive”: cubicle-wear of so-so quality for the single girl in her late twenties whose self-esteem has been almost beaten to death by the beauty-industrial complex, and whose decent education has been punished with a thanklessly demanding office job. She’s a can-do Cinderella who has always had to change the oil in her own pumpkin and is too overworked to have a healthy social life outside the workplace. Her outfits must therefore be corporate-respectable, yet body-conscious enough to attract a nice tax-attorney husband.

The Ann Taylor ethos rubs me the wrong way for the same reason I don’t like white women singing “Summertime” or winos drinking cooking extract: Too much vanilla will make you go blind. But the brand is the retreat position for the schizophrenic D.C. work environment, where female sexuality is both an asset and a liability.

Washington’s permaclass of wealthy Georgetown-establishment socialites has always ruled the roost on D.C.’s domestic front. The older rich ladies are the keepers of the social rulebooks—and the keepers of all the best HUMINT (human intelligence) and RUMINT (rumor-based intelligence) in town. These are the Mean Girls who make or break political aspirations, who get to wear big hats at polo matches, make disparaging comments about social climbers, and police the actions and/or styles of younger, more fertile women.

For a large part, the formalwear created for these women (one of the global teaspoonful of humans capable of affording such garments) is girdled and privileged, highlighting a state of voluntary submission to the patriarchs of their tribe. Their look is an orderly, anger- and yang-free approach to the complex abyss of femininity, drawn from the late 1950s to mid-1960s, when husbands were playboys and closet homosexuals and wives attended luncheons and kept up with correspondence until trotted out for state occasions.

Rich Georgetown ladies tend to drift into that Pat Nixon look that denies that the late sixties ever happened. Their clothes evoke a demure, under-control, decidedly non-rowdy, submissive type of woman who appreciates her role as an ornament of great value, and sits prettily and quietly in Gulfstream jets. It is the look of mothers of brides, and Hong Kong billionaires’ wives. The hard hair and brocade jackets are a throwback to the freeze-dried, declawed, prim, undersexed, shellacked, deodorized, imperial-establishment matron style that always seems to crawl back into women’s fashion during Republican administrations, and tends to coincide with tighter restrictions on women’s reproductive rights, upticks in racism and Bible thumping, and the economic rape of the middle class by “unforeseeable” stock-market calamities that still somehow always seem to massively benefit the nation’s richest 1 percent.

During the darker years of the Bush administration, it struck me that the cut of most women’s clothing in retail fashion inventories eerily evoked Rosemarys Baby. It was all baby-doll dresses and little pastel blouses with Peter Pan collars and smocking over the collarbones. Child-women were infantilized and bowed up until they resembled decorative, virginal Easter eggs. All the high heels seemed to evaporate from department stores in favor of quiet little ballet shoes that might enable a wife to tiptoe out of the dining room so that the men, freshly cigared, could talk like grownups.

There is an indulged weakness evident: The ideal-society wife is made into a streamlined, luxury toddler. Many pieces evoke the Pampered-with-a-capital-P innocence of the nursery, yet defy the vigor of either youth or sex. In the baby-doll dresses, there is no ironic infantilism (that flirty, kinderwhore cuteness that winks at pedophilia), but a kind of learned helplessness that waves a limp hand at actual infirmity—the kind of silky pink-bedjacket garments one imagines Sunny von Bulow wore to sleep through parties.

The creations of designers who cater to First Ladies, such as Valentino, Oscar de la Renta, and newcomers like Derek Lam, tend to be nostalgic and never-challengingly hip. It is a clean, monarchic glamor. The brands have a tenure granted by the designer’s perennial alliances with actual monarchies and the otherwise untouchably rich. In iconography alone, such brands are pure currency: Jackie O. both mourned JFK and married Onassis in Valentino.

When I was first allowed into an Oscar de la Renta boutique, reviewing retail for The New York Times, I found the garments mind-blowing. I clutched the insanely craft-saturated sleeves and stared into them like kaleidoscopes, wondering, “How many nuns went blind?” Layers upon layers of meticulous, eye-crossing detail created a mesmerizing depth of texture. There was so much going on: whole landscapes and leitmotifs wrought in black beads and marabou feathers; drapes and pin-tucks of such alien perfection and accuracy that the dresses looked like they were built by the Pixie Corps of Engineers.

It was there that I saw the point of it all.

Clothing this advanced just might guarantee a lady the center of attention, in most rooms—even if she lacks charm, looks, and substance. It is the haberdashery equivalent of a Maserati; people are likely to be a bit hypnotized, no matter how unspectacular the driver may be.

This article is excerpted from Cintra Wilson’s book, Fear and Clothing: Unbuckling American Style.