IT WAS FASHION week in Milan and a scrum of industry attendees — myself included — were gathered for the debut of Gucci’s new creative director, the Naples-born designer Sabato De Sarno. As the crowd headed into the brand’s creative headquarters, I watched the circus of guests file by, dressed specifically for the occasion: There was a tinsel cape, a gold leather skirt, a vinyl corset, orange goggles, pearl-studded bell-bottoms. There was a man in ruffles the size of palm fronds.

As soon as the new collection’s first look appeared, however, it was clear that Gucci had turned the page on the magpie quirk and maximalist theatricality of its recent past: A clean-cut wool coat with an understated ribbon featuring the brand’s signature red and green stripes was paired with one of Gucci’s most quintessential offerings, its horsebit-adorned loafers, which De Sarno had elevated with a substantial platform. Countless additional runway looks featured the loafers, flat or flatform, giving the models a languorous stride ready for the city streets (where the show would have been held if not for the day’s torrential rain). I looked around and realized I’d originally been distracted by the crowd’s razzle-dazzle — a sizable faction of the audience was actually wearing loafers.

Loafers! The day’s winning choice of shoe was a flat-heeled, low-key, slim-lined classic that’s remained a style staple for nearly a century. “I get stressed putting together looks for these kinds of events,” said a guest I buttonholed about the footwear choice. “But you can’t go wrong with these loafers no matter what you’re dressing for — they’re so iconic.”

The unflashy footwear proved to be a prescient choice: De Sarno’s debut vision of simplified pieces and timeless loafers with trademark Gucci detailing made a distinct if quiet argument for wearable, everyday dressing.

Given fashion’s notoriously fickle character, only a handful of items ever attain the status of an icon — but demand for Gucci loafers has been going strong since they were first introduced in 1953. I had learned that just a week before the aforementioned show when I had the opportunity to examine the loafer in all its historical iterations at the Gucci archive in Florence, where the brand’s collections are preserved in the Renaissance-era Palazzo Settimanni.

Located in the Oltrarno district, Florence’s artisan center for hundreds of years, the historic fifteenth-century Palazzo Settimanni functioned — upon its purchase, also in 1953 — as Gucci’s workshop. When the brand’s needs outstripped the space in the 1970s, it relocated to the nearby community of Scandicci, with additional production done at several factories throughout Italy. The palazzo also hosted Tom Ford’s legendary 1994 debut as Gucci’s creative director, which was a Pitti Uomo runway show featuring plenty of loafers. And it was Ford who began the project of formally chronicling Gucci’s designs. After extensive renovations aided by local artisans restored historical frescos and floors, the palazzo officially opened in 2021 as the brand’s private archive.

My Gucci guide as well as the staff I saw gliding along the cotto ceramic-tiled halls, were all shod in Gucci loafers — black, walnut, even flamingo pink leather. I realized the square-toe shoes I was wearing would probably be out of style in a few years, if not sooner.

When Aldo Gucci took over the family business in 1953, after the death of his father Guccio Gucci, he embarked on an ambitious expansion plan beyond the brand’s Florence hometown, opening shops in Rome, Milan, and New York. Until then, Gucci was known as a luggage maker — Guccio had worked as a bellhop in the opulent Savoy hotel in London, fallen in love with the clientele’s finely made trunks and valises, and launched his namesake luggage brand in 1921 in Florence. Aldo later introduced the loafer as the house’s first footwear with a horsebit to honor his love of horseback riding. The metal detail would soon become synonymous with Gucci itself. At the same time, the brand’s New York boutique opened on 58th Street, and Gucci loafers became the uniform of the well-dressed, with a woman’s version introduced in 1955.

The design built on a long-running American love affair with moccasins. The term moccasin, an Algonquin word that European colonists applied to a vast range of styles found among First Nation and Native American tribes in Canada and the United States, primarily referenced soft leather slip-on varieties whose hand-sewn vamp created a prominently stitched u-shaped toe. Dating back thousands of years, they’re considered the oldest shoe style in existence. Bass introduced Weejuns in 1934, the name alluding to “Norwegian” because they were adapted from a similar type of moccasin associated with the Indigenous Sami people of Norway. These soon became the penny loafers that dominated college campuses across America. The Gucci loafer melded this history with Tuscan leather-working mastery, launching a style that has enraptured generations. As my Gucci archive guide noted, designers in Italy create with a knowledge of craftsmanship. The results are handmade pieces of high artistry which, as I found out when trying on the loafers, slide on like a soft glove with arch support.

As a rare fashion icon, the Gucci loafer has graced the feet of other icons: Jane Birkin, Sophia Loren, Francis Ford Coppola, Brad Pitt, Madonna. And as I held a loafer in pale calfskin leather with a delicately sewn vamp and a smooth-lined shape too refined to ever fall out of favor I understood its staying power — and I promised myself to never buy soon-to-be-passé shoes again.