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    Home»Lifestyle»Ugly, mortifying – and addictive? Tim Dowling’s week in the world’s most divisive shoes | Men’s shoes
    Lifestyle

    Ugly, mortifying – and addictive? Tim Dowling’s week in the world’s most divisive shoes | Men’s shoes

    By Olivia CarterAugust 13, 2025No Comments6 Mins Read0 Views
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    Ugly, mortifying – and addictive? Tim Dowling’s week in the world’s most divisive shoes | Men's shoes
    Toe-curling … Tim Dowling in a pair of barefoot shoes. Photograph: Alicia Canter/The Guardian
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    Back in January, Vogue made a bold headline prediction: “This Freaky-Chic Shoe Will Be Everywhere in 2025”. It had already been spotted on models and rap artists, and all over TikTok and Instagram. By summer, Grazia declared that “The split-toe trend that’s been quietly bubbling for years just hit the mainstream”, citing shopping app Lyst, which named the shoe as one of its top five most-searched items.

    The freaky-chic shoe in question is the toe shoe – a lightweight, thin-soled trainer with separate, articulated toes. They come in a number of brands and styles, and while they may be popular, I can safely say they are not “everywhere”. Walking in them in public every day for a week, I never ran across another person wearing them. Anywhere.

    The original toe shoe is the Vibram FiveFingers, which has actually been with us since 2006. The model I’ve chosen, the V-Alpha Hydro, has a 3mm rubber outsole and a 2mm foam insole, offering a close-to-barefoot walking experience. They’re primarily designed for outdoor training, hiking, barefoot running and general fitness, but they are not designed to look cool. The five separate pockets allow one’s toes to splay out more naturally, if not more attractively. Not for nothing did Vogue call FiveFingers “the fitness world’s most divisive shoe”.

    Vibram is the market leader in a complex footwear category – not all toe shoes are barefoot shoes, and not many barefoot shoes have articulated toes. Some have only a separate big toe, for a more cloven-hoofed look. But they’re all meant to represent an improvement on traditional footwear.

    Tim takes his shoes for a walk. Photograph: Alicia Canter/The Guardian

    The putative benefits listed for my FiveFingers include “zero heel drop keeping you naturally planted to the ground”, “fantastic proprioception and feedback from the feet to the brain” and “as much natural foot movement as possible”.

    The FiveFingers may provide a more natural fit, but that doesn’t mean they fit naturally. My toes don’t automatically slide into their corresponding pouches; they have to be coaxed and prodded in. And yes, if you’re going to wear socks, you’ll need toe socks, adding another layer of complexity to getting dressed in the morning. Even after I think I have my left shoe all the way on, a cursory squeeze of each toe pocket reveals that the second one along is empty. Where did that toe go? It turns out it’s sharing a pouch with its nextdoor neighbour.

    The overwhelming sensation is one of horrifying self-consciousness – these are very weird-looking shoes

    When both shoes are finally on properly, I take them for a brief trial spin. At first, I feel like a circus clown. My splayed toes look like two hands of miniature bananas, and the rubber soles slap against the pavement like duck’s feet. New wearers are advised to transition gradually from regular shoes, because it’s a different style of walking (or running, if that’s your intention). After a cautious 50 metres or so, I settle into a more barefoot stride – mid-foot strike rather than heel strike, and less noisy. Meanwhile, I’m very in touch with the ground beneath me: my toes grip the pavement; I can feel every tiny bump and crack.

    The overwhelming sensation, however, is one of horrifying self-consciousness – these are very weird-looking shoes. No one comments as I walk down a busy shopping street, and after a while I begin to hope no one has noticed – after all, I don’t tend to notice other people’s shoes when I’m out and about. Then I look down and think: yeah, but I would notice these.

    Any remaining hope that my toe shoes are unremarkable is dispelled as soon as I walk into my own kitchen, where my middle son is sitting at the table.

    “What the hell are you wearing?” he says.

    “On my feet, you mean?” I say.

    ‘The fact that I have them on keeps catching me by surprise.’ Photograph: Alicia Canter/The Guardian

    “Yes, on your feet,” he says.

    “The hot girl shoe of summer,” I say.

    My oldest son walks in with his girlfriend.

    “My God, what are those?” she says.

    “The future,” I say.

    “They’re hideous,” he says.

    “They come in other colours,” I say.

    “What are they like to walk in?” she says.

    “Honestly?” I say. “They’re exhausting.”

    They’re so difficult to put on that I’m reluctant to take them off

    This is true: after just a few hours my feet are incredibly tired – not sore or achy, just bone-weary. It takes three days to build up enough tolerance to wear them from morning until night. After that, I hardly notice them. The fact that I have them on keeps catching me by surprise: hey! I think. I’m driving in toe shoes! I’m in a supermarket in toe shoes! I am at one with the earth, intensely aware of tiny changes in the terrain – the grout between the tiles, the dry grass poking between my toes. I’m also getting used to the idea that everyone – everyone – notices.

    My wife is not happy, though, especially when she sees me wearing them just as we’re about to set off for a restaurant.

    “You said a week,” she says.

    “Today is a week,” I say.

    “You really don’t have to wear them tonight,” she says. “You’re just being perverse.”

    The truth is, toe shoes are a little bit addictive: comfortable and light, while also offering a Spider-Man-level of grip. They’re also so difficult to put on I’m reluctant to take them off.

    Once we’re in the restaurant, the shoes stay under the table, and I feel perfectly normal. It’s only as we’re leaving, when I pass a waitress and smile, and she smiles back and looks down, and I see her face change, that I know I can’t go on like this.

    The next day, as I’m posing for Alicia the photographer in my local park, a man comes running over to stop his dog getting into the shot. He apologises, and then looks over at me: a middle-aged man sitting on a bench in the watery morning light.

    “Is it about the shoes?” he says.

    “Of course it’s about the shoes,” I say.

    Do you have an opinion on the issues raised in this article? If you would like to submit a response of up to 300 words by email to be considered for publication in our letters section, please click here.

    addictive divisive Dowlings mens mortifying Shoes Tim ugly week Worlds
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    Olivia Carter
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    Olivia Carter is a staff writer at Verda Post, covering human interest stories, lifestyle features, and community news. Her storytelling captures the voices and issues that shape everyday life.

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