Are loafers in style again?

The preppy staple is back with a vengeance

“I love the fall, and the return to real clothes feels like the real start of my year, even though I’m in my early 60s, so long out of school. Are loafers the right choice for me? I dutifully wore them in my preppy prime in the 1980s, but can I wear them again? If I do: how do I wear them now? Thank you for your assistance” — X, a Reformed Preppy.

Classics endure for a reason: good, solid ideas are the backbone of fashion, and the key to timeless and ageless style. Loafers have taken almost a 10-year break from the major trend cycle, since the last revival circa 2012. But this fall, they are back with a vengeance, fuelled by a generation to whom the look is entirely new.

The keen young women in their spanking new lug-soled Prada-esque loafers will indeed have to share this trend, because loafer life is for everyone. Dear Reformed Preppy, there is just one person I would consider calling to help break down for you the fashion semantics of the loafer, their history and a fresh take on how to wear them now: Susie Sheffman is a respected fashion editor with decades of experience at the top of her field and she is a lifelong loafer devotee herself. As a bonus, she also does the creative direction on Browns Shoes campaigns, so she did her thinking about this season long ago.

“I’m such a loafer girl, from birth!” she says. “My earliest memories are of walking to school, skipping and scraping the heels of my penny loafers along the sidewalk.”

September, she says, always meant a fresh pair of loafers. “We would shuffle off to Buffalo,” she says, to buy new ones at the border outlets.

“They never went out of style,” says Sheffman. “There is a certain kind of quintessential, classic style babe who has always worn them.”

But why are they so ubiquitous again? “There are so many factors converging.

For one, the sneaker thing has been going on for so long,” she says. This is just as easy a look — you slip on loafers after all — and the context is the same. “Fresh look, same vibe. Any time you were going to reach for sneakers, you can now reach for loafers instead. It’s just a more polished way to leave the house, but with the same appeal: no laces, you don’t have to bend down.” Call it a gentle re-entry to hard shoes.

The main difference this fall, says Sheffman, is the sock. The years of bare feet and loafers are over. More later on the exact nature of the socks to seek now and the subtleties of hemline adjustments; first, let’s look at how we got here and what conclusions we can draw about the trend cycles to figure out: why loafers and why now?

Sheffman shares the fashion bedtime story of the origin of the loafer, beginning with the Bass Weejun, the OG loafer label that is still around, virtually unchanged and a very valid fashion choice still today. “Rich young Americans in the early 1930s were wandering around Europe,” she says. “They admired the shoes on the feet of Norwegian fishermen.” The Weejun name is a phoneticization of “wegian.” The shoe became an instant classic for men, immediately co-opted by women who were taken by its practicality. The penny in the loafer, BTW, was for practical purposes: to keep coins handy to make calls from phone boxes! The preppies of the ’80s filled the little coin slot in the vamp of their loafers with silver pieces, in testament to the greed decade.

But that is skipping ahead of the postwar ’50s, when loafers became synonymous with elegance — from James Dean to JFK, stylish men punctuated their trousers with a crisp loafer. Sheffman swoons at her favourite ever loafer moment, as seen on Grace Kelly, at the end of 1954’s “Rear Window”: “She’s lounging on a couch with a man’s red buttondown shirt and jeans rolled up at the ankle, wearing a perfect pair of loafers, reading a book on the Himalayas.”

Around the same time, a loafer revolution was happening in Italy. The 1950s were when Gucci first nodded to equestrian style with the horse-bit hardware that upgraded loafers into fashion statements; today the revived 1953 Horsebit Loafer is a top seller. Since Alessandro Michele took over as creative director at Gucci in 2015 (actually, before that, because he was in charge of accessories in the decade before his ascent to the top of the label), the Gucci loafer has become an unstoppable reissued and continually updated icon.

Twists on the hardware theme — chains, logo plaques, grosgrain ribbons across the vamp — have become constants at other Italian houses, such as Ferragamo, and at Tod’s, home of the driving moccasin, kissing cousin to the loafer.

Miuccia Prada has been riffing on iterations of her own loafer styles — often with the thick, showy lug sole the brand is currently favouring — since she expanded her family heritage luggage brand into a full womenswear line in 1989. In fact, it is Prada’s “jolie laide” or “ugly beautiful” esthetic that underscores the current way to wear loafers, says Sheffman, which is a distillation of “nerdy chic.”

So, with a legacy of both humble and slick, the loafer feels about right once again for the vast contradictions of life in 2021. “They did become an international symbol of elegance and wealth,” says Sheffman, but at the same time they are egalitarian and everyone can wear them.

“There are a lot of options right now: coloured, two-toned, faux snake or croc, but the lug sole is the fashion-forward way to go,” says Sheffman.

She loves a slick black loafer, or an all-year white or cream loafer, or what she calls cordovan (a classic burgundy), with caramel as another great everyday investment. But rainbow bolds and driving moccasins can be a fun, novelty choice, too.

Younger people, she says, “will be wearing them hard with something soft, as in loafers with a floaty midi-dress or skirt.”