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.