Why loafers will always be the ultimate luxury shoe

To measure the prestige of ultrachic Gucci Creative Director Alessandro Michele, you could look up the brand's surging sales figures and enraptured runway reviews. Alternatively, you could look down at the feet of your fellow pedestrians, at least in dressier circles.

You'll notice no shortage of loafers adorned with the house's signature horse bit. Among those, you'll spot new eye-catching versions enriched with Michele's ­phantasmagoric visions: embroidered honeybees, appliquéd serpents, and metallic-leather Union Jacks.

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It's a great moment for the Gucci bit loafer, and thus for all loafers, arguably the official footwear of globalism – inspired by the Iroquois, invented in Scandinavia, mass-produced in America, refined in Italy, and now worn at Davos.

Playboys and prepsters

The Gucci staple is still a crucial point of style overlap between the uniforms of European playboys and American prepsters. Favoured since the 1960s by Wall Street bankers and K Street lobbyists, it's a significant cultural artifact, a versatile accessory, and not necessarily a walking-around shoe. In June, during the menswear trade show Pitti Uomo, I witnessed a hot debate about Gucci loafers at Caffe Gilli, a Florence restaurant that during Pitti transforms into a gurgling fountain of Aperol spritz. Each of the debaters was a fashion type who'd picked up his bit loafers the year before. One guy described the breaking-in process as no big deal – they felt as soft as silk from the first. The other described it in profane terms, cursing the blisters raised by his rush to keep in step with trends.

Loafers in general, in this era of loosening office dress ­standards, still stand firm. G.H. Bass & Co. Weejuns, the American uncle of the Gucci shoe, has proved just as persistent. Made in Wilton, Me., since 1936, Weejuns are named after a Norwegian shoemaker who himself had copied Native American moccasins. In the mid-20th century heyday of the Ivy League look, Weejuns penny loafers had a ­wearing-pajamas-to-class aura of loungewear cool.

Tough and tasseled

Weejuns are notoriously tough to break in, even more so than the Gucci bit loafer. Some owners, on ­acquiring a pair, habitually pad around the house wearing them with thick socks – or treat the insides with Vaseline or even stick them under the mattress, as if they're baseball gloves. A hedge funder friend of mine once made the error of wearing a box-fresh pair of Weejuns on a four-day roadshow. It ended with him crippled, requiring cab rides to go two blocks.

The tassel loafer took off in the 1950s, broadly popularised then by the Alden Shoe Co., and these days it's revered among a more precious set of lads. A lot of the guys who wore them back in the day are still kicking, and on those dandies a tassel loafer looks adorably dapper and dancerly. But in some conservative offices, the flourish is verboten. Delightfully disreputable, even.

Gentlemen who believe the tassel doesn't go far enough sometimes slip boldly into a Tod's kiltie, which boasts a fringed saddle. The kiltie, loud and grossly ­grandiose, is favoured by slick-haired polo-shirt-tuckers – and by blowhards holding court at the country club bar. But don't write it off for yourself, demure steppers. If the shoe captures your imagination, follow the lead of those wild clotheshorses who balance its extravagance by wearing it with a rather casual outfit, an extremely nonchalant attitude, and, most important, bare ankles.

The sock-free movement

On that note, I'll close with an anecdote from Diego Rossetti, president of the Milan-based shoemaker Fratelli Rossetti SpA, which makes the unadorned style called a Venetian. He claims that his father, who founded the company in 1953, single-ankledly made it fashionable to wear loafers without socks.

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"He was supplying shoes to Italian suitmakers for ready-to-wear shows," Rossetti recalls. "I remember doing a show where the tailor was showing the men on the runway with no tie – without even an undershirt. He said, 'If we can get rid of the undershirt, we can get rid of the sock.' Now it seems normality, but that was very unusual."

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Check out the gallery above to see some of the best loafers for men.

Executive Style