What happens when artificial intelligence meets old money manners, style, and lifestyle? In this witty and insightful episode of Awkward Etiquette: Old Money & New Manners, Kiki Astor takes on the rise of the AI Old Money Girl — that picture-perfect, algorithm-crafted vision of luxury and composure who seems to live in a permanent Ralph Lauren ad. She’s flawless, serene, and utterly unreal. She's also damaging to your self esteem and your sense of reality.

Here's the thing: true sophistication isn’t generated — it’s cultivated. Kiki explores how to use AI tools elegantly, not for artifice but for authentic refinement. From organizing your wardrobe like an old-money heiress to planning seamless travel, writing better thank-you notes, hosting with warmth, or even curating digital routines that feel intentional — this episode is your guide to living beautifully in the modern age.

You’ll learn how to blend technology with timeless taste, how to stay discerning amid digital perfection, and how to make AI your most stylish assistant — not your aesthetic enemy. Because real elegance, luxury, and grace were never about resisting innovation… they were about mastering it, beautifully.

"People will talk."

For ages, this has been used as an excuse for not doing something that could be incredibly rewarding, be it starting a business, writing that book, making the art, or wearing the dress or the lipstick that makes your heart sing.

In this week’s episode of Awkward Etiquette- Old Money and New Manners, Kiki Astor explores one of the oldest social anxieties in the book: what people say about us—and why it still stings, even - or esecially- in the age of curated feeds and public personas. From the elegant discretion of old money circles to the performative transparency of modern social media, Kiki dissects the etiquette of reputation, how to navigate gossip gracefully, and why not caring what others think is the most powerful (and chic) move of all, and a social skill you'll want to develop as soon as possible.

Listeners will learn how to protect their reputation without becoming paranoid, reclaim their narrative with composure, and turn criticism into quiet confidence. Kiki also unpacks how online notoriety has changed the rules of reputation—what still matters, what doesn’t, and how to maintain dignity, mystique, and good manners even when “people will talk.”

It’s a witty, psychological, and oddly reassuring guide to surviving the spotlight—whether it’s the country club, the comments section, or your own circle of frenemies.

Hosting doesn’t have to be hard — unless, of course, you make the tragic mistake of calling it a potluck. In this sparkling episode of Awkward Etiquette: Old Money & New Manners, Kiki Astor reveals the secrets of easy entertaining the old money way. From what to wear as a host or hostess to the timeless menu formulas that never fail, Kiki shares how to create effortless elegance (even on a budget).

Expect chic dinner party ideas, old money anecdotes, and the kind of practical charm that transforms chaos into calm. You’ll learn why gracious hosting is less about perfection and more about good manners, atmosphere, and the right lighting. Whether you’re planning a weekend luncheon or a supper for six, this episode is your guide to sophisticated entertaining with wit, warmth, and a dash of scandalous truth.

Topics include: old money entertaining, hosting on a budget, elegant dinner menus, what to wear when hosting, modern etiquette for hosts, and how to throw a proper dinner without losing your mind.

Beauty fades. Fortunes vanish. But style—the kind old money has mastered—is eternal. In this week’s episode of Awkward Etiquette with Kiki Astor, we unravel the old money secret to staying unforgettable long after the roses wilt and the cheekbones soften. From patched Barbour jackets to grande dames in caftans, from Brooke Astor’s birthday notes to Diana Vreeland’s “garden in hell” apartment, this episode explores how true style outlasts both beauty and wealth.

We’ll meet the archetypes of age and authority—the Dowager, the Grande Dame, the Patriarch, the Patron, the Spinster Aunt, and more—each a living proof that permanence comes not from youth, but from cultivating eccentricity, rituals, and presence. Along the way, you’ll discover why old money never throws anything away, how to turn quirks into calling cards, and the simple rituals you can borrow to make yourself unforgettable in a disposable age.

If you’ve ever wondered why the old money aesthetic keeps trending—or how to build a style that even time can’t erase—this is the episode for you.

What makes a home look quietly elegant… and what makes it look like a Cheesecake Factory in disguise? In this episode, Kiki Astor breaks down the common, supposedly “old money” decorating elements that actually cheapen a house when done wrong.

From blinding white exteriors and shiny DIY lacquer walls to overdone marble countertops in modern farmhouse McMansions and Greek columns that aim to make a 60's ranch-style home look like a neo-Palladian estate but instead fall painfully flat, Kiki explains why these popular choices fail — and how true old money interiors whisper rather than scream. Drawing on the lessons of icons like Billy Baldwin, Tony Duquette, Bunny Mellon, Nina Campbell, and Ralph Lauren, she reveals the timeless principles of proportion, context, and patience that create authentic elegance. But don't worry if your home was built in this decade rather than inherited from Gilded Age great-grandparents, we have some savvy budget-minded tricks in this episode that will surprise you- and even some shocking hacks that you won't believe.

Expect sharp insights, a few scandalous design confessions, and plenty of cheeky etiquette along the way, including working with a friend who is a decorator. Whether you’re dreaming of old money style, redecorating on a budget, or just curious about the fine line between tasteful and tacky, this episode is your field guide to avoiding the most common “new money” décor mistakes.

What happens when ordinary people become multi-millionaires overnight? In this episode of Awkward Etiquette with Kiki Astor, we explore the lessons people who come into an unexpected fortune can learn from old money families about handling sudden wealth with grace, restraint, and dignity.

Whether you inherited a lot of money, are a lottery winner, a successful entrepreneur or entertainer, or had a similar financial windfall, Kiki unpacks the essential etiquette of newfound fortune: what to spend on (and what not to), how to avoid the biggest mistakes lottery winners make, and why appearances of restraint often matter more than flashy purchases. She also shares timeless strategies for dealing with friends and family who ask for money, guidelines for giving to charity without turning yourself into a public ATM, and how to build a lifestyle that lasts longer than a single windfall.

Whether you’re daydreaming about winning Powerball, navigating an inheritance, or just curious how the wealthy maintain their composure, this episode offers witty, practical advice on how to live richly—without losing your head.