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Along the way, they had become powerful stalwarts — if not political mascots — in their districts: Ms. Maloney, a pathbreaking feminist and the widow of an investment banker, represents an East Side district so wealthy it was once christened the silk-stocking district; Mr. Nadler, a proudly opinionated old-school progressive, holds down the West Side.

“It was a silk-stocking church, so to speak. The people had good government jobs. The ministers preached to the head and to the heart.”

Structurally, James’s journey is reflected through the plodding histories of the famous silk-stocking women he intersected with, and as a result the designer’s own image never fully fills the mirror.

Bush was a silk-stocking Yankee of high privilege while Reagan was an outsider from the Midwest who grew up in a modest home.

Miles, she said, comes “from corporate America” and has spent much of his career “hob-knobbing with CEOs and working at silk-stocking firms. … You don’t really see the ground-eye view to know the people out there who are really suffering and who need protection from the AG the most.”