Before November, what a different experience it would be reading "Lillian Boxfish Takes a Walk," the new novel from poet, essayist and memoirist Kathleen Rooney. With expectations of a Pantsuiter-in-Chief, unrivaled policy wonk and master of the shoulder shimmy, we could glance safely back at the bad old days when few women achieved career success and those who did were undercompensated and otherwise horribly treated.

Rooney touches on these injustices in "Lillian Boxfish Takes a Walk," a frequently charming novel inspired by the career of Margaret Fishback, a pioneering and highly successful ad copywriter for Macy's in the 1920s and 1930s. Like Fishback, young Lillian Boxfish heads to Manhattan to forge a self, going on to publish volumes of light verse in addition to establishing a stellar advertising career.

The reader first meets Lillian, however, at age 85. It's New Year's Eve 1984, and she's bound for a trek around Manhattan togged out in mink coat and mustard-yellow stockings. Her Big Apple is far less sanitized than today's, with spiking crime rates and the Subway Vigilante still at large after shooting four black youths who allegedly asked him for $5. But Lillian is undeterred. Off she goes, forging connections along the way and reflecting on her life.

As the evening progresses, she meets barmen, restaurateurs and bodega clerks; parties with young artists, and converses with three boys who ask her for $5. In memory, young Lillian falls hard for Manhattan during the Jazz Age, taking lovers, feuding with inept colleagues and futilely cajoling her boss for equal pay. Prohibition is law, and she liquors up in neighborhood speakeasies, with "friends of friends gently embalming themselves in alcohol, curing themselves like wild game in cigarette smoke."

From early days in the Macy's ad department she takes lunch-hour rambles, passing under the now-defunct 6th Avenue Elevated: "Chow mein restaurants and diners with names like The Griddle. Cinders and ash and noise sifting down, shaking the ground, rattling the buildings. … Commuters getting disgorged at one of the overhead stops dislodged a deposit of pigeons like a plume of smoke."

Lillian's story spans most of the 20th century, touching on racism, the AIDS crisis, immigration and women's rights, but Lillian Boxfish is more ode to flânerie or slant screwball comedy than historical novel or social critique. Despite her brilliance, we learn, Lillian never achieves earning parity, is forced out of a job during pregnancy and — like Margaret Fishback — would have faced regular workplace harassment, yet her story often lacks friction. Even her wrenching personal troubles develop largely offstage.

Such omissions keep our self-assured heroine firmly in command as she strolls the city streets, but the novel is weaker for its uniform tone and averted conflict.

Marian Ryan's work has appeared in Slate, Salon, the Los Angeles Review of Books, the Mail on Sunday and other publications.

Lillian Boxfish Takes a Walk
By: Kathleen Rooney.
Publisher: St. Martin's Press, 287 pages, $25.99.