Why We Hate It

Putting your initials on your belongings was a practical, refined move—for those who lived more than a century ago. “In the late-19th century, monograms became something that people added to undergarments and household linens,” said Kristina Haugland, the Le Vine associate curator of costume and textiles at the Philadelphia Museum of Art. “It was a way of marking things that were sent out to be laundered so you could get them back, because they were valuable.” Monograms eventually became status symbols, said Ms. Haugland. It was expensive to put your mark on everything.

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Similarly, with the rise of leisure travel among the upper crust, leather-goods purveyors like Louis Vuitton and Goyard started to paint owners’ initials on trunks to avoid a mix-up in baggage claim. (Nothing ruins a trip like having to send the butler out to replace your boxers.)

Today, however, when anyone can get almost anything monogrammed or otherwise personalized, the cachet has collapsed. At Gucci, clients can stamp their initials on purchases from leather sneakers to studded biker jackets, while J. Crew has an entire monogram shop devoted to stitching your initials on buttons-downs, belts, T-shirts and bikini bottoms. Want to flash your letters on your Frame jeans? Step right up. When considered alone, any one of the above has its charms, but taken as a whole, it’s clear personalization has lost its specialness—and sense of exclusivity. Thanks to Etsy, you can even get your initials or name on plastic shower curtains, a wooden cutting board...the silliness knows no bounds.

“What started out as a very personal act now just feels generic,” said Rose Pilato, a beauty publicist in New York who most often says “no” to monograms. “Just because the option is there to add your initials doesn’t mean you should do it.” Anonymity has never sounded quite so chic.

Why We Love It

When done in a modern and unexpected way, a monogram instantly adds interest to a simple item. Take the cozy cashmere sweaters personalized with extra-large cursive initials by New York knitwear brand Naadam.The oversize 380-point font, said Naadam CEO and founder Matt Scanlan, “pokes fun at the monogram. It’s over-the-top and kitschy.”

Mr. Scanlan’s irreverent take on the tradition, with its shades of “Laverne & Shirley,” has been a hit among influential women like Glossier CEO and founder Emily Weiss. “After Emily wore hers, we were getting 100 to 200 requests a day,” said Mr. Scanlan. He is seriously considering installing an embroidery machine and technician in the brand’s office to keep up with demand.

Sporting your name or initials in an obviously self-aware, wink-wink way can reinvigorate this tired trend. While Lady Mary of “Downton Abbey” would never have carried a sparkly evening bag emblazoned with “Mrs. Crawley” in 300-point type, Edie Parker designer Brett Heyman has found many clients for her customizable box clutches. That said, Ms. Heyman will soon offer a font that’s about 80% smaller. “Sometimes you want to be a little more restrained,” she said.

Certainly Ralph Lauren is poking at least a bit of fun at monogramming’s history with its new hyperbolically aristocratic personalized crests. (Take that, Duchess! Anyone can be royalty now.) They’re available in six styles, which can be stitched onto blazers or polo shirts.

Even with arguably cool monograms, moderation is key. “It should be one moment in an outfit,” advised blogger and design expert Erica Domesek, whose initials E.L.D. are a big part of her identity. (“It’s my nickname and how I sign my emails.”) Ms. Domesek said she might wear her bespoke Naadam sweater with black jeans and plain Gucci loafers but leave the monogrammed L.L. Bean tote at home. “It’s a chic nod,” she said, “never anything that’s overdone.”

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