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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this episode of Awkward Etiquette with Kiki Astor, yes, we’re breaking down the myths behind the old money aesthetic- but we're sharing the secrets of all effortlessly stylish people. Think you can buy the uniform and waltz into the club? Think again. Kiki explores the difference between curating and cosplaying, and why real style can’t (always) be Amazon-Primed.
We dive into the psychology behind inherited clothes and inherited neuroses, and how to decode your upbringing to find your true personal style. Why does new money often look so...tacky? Why do old money wardrobes (and homes) have that quiet, undone charm? It’s not about perfection—it’s about patina over polish, heritage over hype.
With nods to Carolyn Bessette’s secret sauce, Kiki shows you how to train your eye, embrace imperfection, and stop copying starter packs in favor of becoming a classic in progress. Because style—real style—is lived in, layered, and entirely yours.
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