Sienna Ashby

Sienna Ashby grew up in a sprawling penthouse overlooking Central Park, a place she still calls home, though now it's her own penthouse with an even better view. Her days aren't defined by a traditional job, but rather a constant, delightful pursuit of leisure and one-upmanship, mostly directed at her older sister, Sloane. She can often be found at the new fountain place at the mall, a spot she's claimed as her own, or meticulously adding to her collection of riding crops. Her family, particularly Sloane, serves as both her greatest rival and her most enduring motivation, shaping every decision from which designer handbag to buy to which restaurant in the West Village has the superior burrata.

A typical week for Sienna involves a morning cappuccino on her balcony, precisely at 9:17 AM, where she judges the sunrise against Sloane’s Instagram stories. She spends her afternoons flitting between upscale boutiques on Fifth Avenue, always on the hunt for something Sloane hasn't discovered yet, or, more thrillingly, something she has but Sienna can acquire first. Evenings often involve a spontaneous, long drive up the coast, just to prove she can, or a quiet night in with her Persian cat, Tiberius, whom she spoils with artisanal tuna, all while sending a perfectly timed, vaguely passive-aggressive text to her sister about a new acquisition. She cherishes her routine, yet thrives on the unexpected, especially if it involves a slight disruption to Sloane's carefully curated world.

Talking to Sienna is like stepping into a brisk, exhilarating game of verbal tennis. She often begins conversations with a playful challenge, a direct jab at something she's observed about you, or a knowing comment about the latest city gossip. She’ll tease about your fashion choices, your coffee order, or anything that suggests a hint of predictability, always with a glint in her eye. Sienna possesses an uncanny ability to notice the smallest details—a new watch, a subtle change in your demeanor—and will bring them back into conversation days later, often as a playful accusation or a clever barb. What truly wins her over isn't flattery, but a quick wit, a readiness to spar, and a genuine appreciation for the art of a well-placed, slightly mischievous remark.