Timeless or Tired? The Old Money Aesthetic in 2025
Awkward Etiquette With Kiki Astor
Release Date: 01/06/2025
Awkward Etiquette Season 4 ep 3
Awkward Etiquette With Kiki Astor
Looking to marry up, move up, or simply mix with high society—without getting laughed out of the room? In this episode of Awkward Etiquette, Kiki Astor pulls back the velvet curtain on modern social climbing and how to do it with grace, discretion, and strategic charm. Whether you're angling for a seat at the boardroom table, a place in the Hamptons, or just a better table at Cipriani, this is your cheat sheet to elegant upward mobility. We’ll cover: The unspoken rules of old money circles, new money power networks, and the high-level corporate elite How to cultivate access and influence...
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Summer Entertaining Secrets: The Old Money Style on a Budget Guide
Awkward Etiquette With Kiki Astor
In this episode of Awkward Etiquette with Kiki Astor, your Auntie Kiki spills a whole chilled bottle of rosé worth of her best secrets on how to entertain with true old money elegance—no villa or vintage yacht required. From Newport-style lawn luncheons to boho-glam back garden soirées, learn the etiquette commandments of summer hosting: think linen chic dress codes, room-temp bites, and shady seats (always!). Listen in as Kiki dishes on everything from Dalí’s surrealist dinners and the mythic Riviera summers of the Murphys, to mosquito repellents that double as accessories and the art...
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Old Money, Open Doors: The Glamour and Guilt of Hosting & Houseguests
Awkward Etiquette With Kiki Astor
This week on Awkward Etiquette with Kiki Astor, we’re diving into the enduring—and often awkward—tradition of the summer houseguest. From the Gilded Age to the Hamptons, summer hosting has long been a cornerstone of old money etiquette and upper-class rituals. But why did houseguests used to stay for weeks (or even months)? And how can you survive it today—whether you’re the host or the one unpacking in someone else’s guest room? Kiki shares the surprisingly elegant history behind long-term summer guests, the unspoken codes of how to be a good houseguest (and host), and what to do...
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How to Disaster-Proof "I Do": Kiki Astor's Best Wedding Etiquette Tips
Awkward Etiquette With Kiki Astor
Planning a wedding? Attending one? Praying your drunk uncle doesn’t grab the mic during the toasts? You’ve come to the right place. In this episode of Awkward Etiquette with Kiki Astor, we unpack the unspoken rules and social slip-ups that can turn a dream wedding into a diamond-studded disaster. Whether you’re the blushing bride, the groom with opinions, the mother-in-law with a seating chart grudge, or just a guest determined not to wear white (again), this guide to modern wedding etiquette will help you glide through the season with grace, style, and minimal scandal. From guest list...
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No Trust Fund, No Problem: How to summer like an Astor on any budget
Awkward Etiquette With Kiki Astor
In this sun-soaked episode of Awkward Etiquette with Kiki Astor, we unpack the storied tradition of “summering” in old money circles—from Newport to Nantucket, the Hamptons to the Highlands. Kiki dives into the social history behind the season: why certain destinations became icons of understated wealth, how WASPs made “going to the country” a ritual of quiet luxury, and what distinguishes a legacy summer spot from a flashy one. You’ll learn: The defining characteristics of old money vacation spots, and the key packing list items for each The etiquette (and quiet codes) of...
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Forks, Fermented Fish, and Faux Pas: Etiquette and Table Manners for the Old Money Set
Awkward Etiquette With Kiki Astor
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Monogram Etiquette, Style, Tradition, and Rules: old money preppy, or tacky?
Awkward Etiquette With Kiki Astor
In this episode of Awkward Etiquette with Kiki Astor, we tackle the timeless, tasteful, and occasionally tacky world of monograms. From heirloom linens to luggage tags, monogramming is the original quiet luxury flex—if you know how to do it right. Kiki explores the history of monograms, their role in old money culture, and the subtle etiquette rules that separate timeless from tacky. Think: Where should your initials go? How many things can you monogram before it’s a crisis? Should couples share a monogram? (Spoiler: not always.) We’ll decode the do’s and don’ts of personalizing...
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The old money photography secrets Slim Aarons knew (and you may not)
Awkward Etiquette With Kiki Astor
Today, we’re turning our lens—quite literally—toward the fascinating intersection of photography and old money. From the earliest daguerreotypes in stiff collars to the poolside glamour captured by Slim Aarons, photography has always been a mirror, revealing not just what we look like—but who we *think* we are. We’ll begin with a little history: how photography was once the domain of the upper class, with hand-colored portraits and family albums kept under lock and key, and how the arrival of the Kodak changed everything—from debutante balls to Riviera summers. Then...
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Table for one, please: the lost art of intentional, elegant solitude
Awkward Etiquette With Kiki Astor
In this elegantly introspective episode of Awkward Etiquette with Kiki Astor, etiquette expert and romance author Kiki explores the timeless allure and quiet power of solitude. From the romance novel heroine brooding on a windswept terrace to the old money doyenne dining solo in a tucked-away bistro, being alone is not a condition to be pitied—it’s an art to be mastered. Kiki delves into the etiquette of spending time alone with intention and elegance, whether you’re reading on a park bench, traveling solo, or savoring a quiet meal at a fine restaurant. Learn how to navigate the manners...
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Heritage or hype? The true value of luxury handbags in 2025: an old money perspective
Awkward Etiquette With Kiki Astor
In this episode of Awkward Etiquette with Kiki Astor, we dive into the true value of luxury goods—especially designer handbags—amid a shifting global economy, social media overexposure, and growing transparency about where and how these so-called “heritage pieces” are actually made. In the age of the Wirkin, or Walmart Birkin, and in the wake of the Chinese revealing exactly how many luxury goods get produced in their factories rather than in chic Parisian ateliers, Kiki unpacks (pun very much intended) the history of handbags as status symbols, from old money necessity to nouveau...
info_outlineNew Year, New You... So is the Old Money Aesthetic Out? How does one reconcile reinvention and tradition?
In this first of the New Year episode of Awkward Etiquette with Kiki Astor, we explore the tension between tradition and reinvention in the ever-evolving world of the old money aesthetic. Kiki talks about her New Year's resolutions and goals, and delves into the delicate balance of maintaining timeless elegance while embracing the excitement and potential of a fresh new year. Listeners will learn how to romanticize their lives in a meaningful, authentic way, on a budjet, naturally, stay true to their values, grow as a person, and stay graceful, fashionable, and elegant in the face of change, all while adhering to the understated luxury that defines the old money ethos, which is, spoiler alert, very much not over. Engage with us as we discuss elegant New Year’s resolutions and the art of navigating reinvention with poise and confidence.