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 drama and overbearing family members to dress codes, RSVP protocol, emotional outbursts, and the etiquette of elopements, Kiki offers practical advice and sly commentary with old money polish and new manners wit. Plus: how to behave at the reception, what to never say during a toast, and why good etiquette is the best insurance policy for your “I do.” You'll also be getting stories from Auntie Kiki's long-ago wedding.

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 classic summering culture

• Key destinations like Bar Harbor, Watch Hill, Gstaad, and Cap d’Antibes—and what they signal socially, and how to romanticize your life until it really does feel like you're summering there

• How to channel old money summer vibes with elegance and humor, even if you’re staycationing, house-sitting, or renting the cheapest French Riviera adjacent flat.

This isn't just about faking it til you make it, it's about curating summer rituals and enjoying the experiences that will leave you feeling refreshed and inspired come fall, even if your only vacation was a staycation.

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 everything from stationery to sleepwear, and examine why the old guard swears by embroidery while the nouveau crowd goes straight for logo overload.

Whether you’re wondering how to monogram a dinner napkin or considering your married monogram before there’s even a ring—this episode is your ultimate guide to monogramming with elegance, restraint, and just the right amount of self-regard.

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 we’ll tiptoe into modern-day etiquette: how to take a photo without looking like a try-hard influencer, when it’s actually charming to ask for a picture, and why certain kinds of candids will always feel more elegant than a staged selfie in a wine cave.

And of course, we’ll spend time with the master of leisure himself: Slim Aarons. His lens didn’t just capture old money—it *created* its mythology. From sun-drenched villas in Capri to Ivy League tailgates, he defined what it meant to live “attractive lives in attractive places,” and he did it with a sense of ease, charm, and just enough detachment.

Finally, I’ll share how to take your *own* iconic photos—yes, you too can look like a Kennedy on the Cape, even if you took the ferry—and how to display your images at home so they feel like heirlooms, not dorm room décor. Think archival mats, subtle frames, and a gallery wall that whispers rather than shouts.

So put down your ring light, pour yourself a weak gin and tonic, and let’s dive into the art of appearing timeless on film.

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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 of solo dining, embrace the understated glamour of doing things alone, and reframe solitude not as loneliness, but as personal luxury. With references to iconic solitary figures—think Jackie O, Greta Garbo, and mysterious heiresses who summered alone in the South of France—this episode is a cheeky-yet-chic guide to becoming effortlessly comfortable in your own company.

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 riche billboard, and dissects the old money perspective on luxury: discreet, enduring, and never desperate.

With juicy anecdotes from her recent travels through Morocco, Turkey, and China, Kiki shares firsthand observations of the proliferation of fake designer bags, the depressing state of luxury duty-free shops, and the disillusioning reality of modern production—even at historic maisons like Hermès and Chanel.

Topics we cover:

• The erosion of luxury's mystique in the age of TikTok unboxings.

• Why handbag resale value isn’t the flex people think it is.

• How discerning old money treats luxury goods (hint: if it has a TikTok hashtag, it’s already over).

• Spotting a dupe without losing your mind (or your manners).

Whether you're a bag lover, a social climber, or simply etiquette-curious, this episode is your guide to navigating the luxury landscape with wit, wisdom, and perspective.

If you suffer from social anxiety, you might think that the old money, high society types you see effortlessly navigayting cocktail parties were simply born with a socializing superpower, or that they learned it in boarding school, and that it's too late for you, but that's not true. In this calming yet cheeky episode of Awkward Etiquette with Kiki Astor, Kiki turns her velvet gloves toward a topic near and dear to many hearts: social anxiety. Whether you freeze at cocktail parties, overthink every interaction, or find yourself replaying conversations in bed at night, this episode is your invitation to breathe, settle in with something fizzy or soothing, and reclaim your social confidence—the elegant way.

Kiki reveals her favorite etiquette-based social skills hacks designed for introverts, overthinkers, and those who never know what to do with their hands. You’ll learn how classic etiquette tricks—like the art of introductions, small talk that isn’t painful, and exiting a conversation gracefully—aren’t about perfection, but about making others feel comfortable, which (spoiler alert) helps you feel more at ease too.

From how to glide through a room without breaking a sweat to using etiquette as armor in awkward social situations, Kiki shows that even the most anxious among us can master the social graces of high society—without faking a thing.

Perfect for:
Anyone looking for social anxiety tips, introvert-friendly social strategies, and a little old-school etiquette wisdom with a wink.