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.