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Why the loafer’s chic style remains a favourite, with Gucci, Prada and Miu Miu presenting their takes

STORYAnnie Brown
Etymology loafers. Photo: Handout
Etymology loafers. Photo: Handout
Fashion

The loafer’s punk-to-preppy versatility makes the shoe a hit among celebs from Cary Grant to ‘It’ girls like Hailey Bieber and Kendall Jenner

Loafers, worn by everyone from timeless style icon Cary Grant to “It” girls like Hailey Bieber and Kendall Jenner, have an interesting and somewhat disputed origin story.
Christian Louboutin Penny leather loafers. Photo: Mytheresa
Christian Louboutin Penny leather loafers. Photo: Mytheresa
Depending on who you ask, they are attributed to Norwegian peasant fishers and farmers, or the moccasins worn by Native Americans. Brands such as Maine’s GH Bass, meanwhile, are credited with creating a new kind of loafer, the Weejun, in the 1930s and making it the must-have piece for Ivy League students. The “whale tail” strap at the front of the Weejun had space for a penny – and while some have said it was put there to have a handy coin for emergency phone calls, mostly it was a mere style statement.
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In any case, “penny loafers” – spied on recent runways such as Prada and Miu Miu – have lost none of their appeal in the years since. Indeed, the humble loafer in all its iterations, whether worn by bankers and preppies, cool girls or stylish nerds, is yet again one of the year’s biggest shoe trends.

Tod’s loafers. Photo: Handout
Tod’s loafers. Photo: Handout

Sydney-based celebrity stylist Jessica Pecoraro says there’s much to like about their versatility. “What I love most about loafers is their chameleon-like quality: that a single pair can be worn to countless occasions, transforming completely depending on what you choose to style them with,” she says.

Pecoraro likes to wear them with both a relaxed suit, and a tried-and-true jeans and blazer combination. “To push the look in a more fashion-forward direction, experiment with ribbed socks or statement hosiery for something playful,” she says.

Phoebe Philo Club Loafers from Sourcewhere. Photo: Handout
Phoebe Philo Club Loafers from Sourcewhere. Photo: Handout
A word of warning though, the loafer and white socks look – a nod to preppy stylings of the 1950s and worn by the likes of Paul Mescal with his Gucci loafers and tiny shorts, and Natalie Portman on the set of Lena Dunham’s Good Sex (not to mention every man at the local natural wine bar and on TikTok) is not for everyone.

As New York-based writer and man about town Derek Blasberg recently wrote on his Substack “And Another Thing”, “Is it ageist of me to say that at a certain point in a man or woman’s life, he or she can no longer do this trend of white socks and penny loafers with a skirt or shorts?” Gabriel Abi-Saab, co-founder and creative director of Australian shoe brand Etymology, believes there’s an art to wearing loafers well.

The Row eel loafers from Sourcewhere. Photo: Handout
The Row eel loafers from Sourcewhere. Photo: Handout
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