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Kendall & Co.: A Masterclass in Calculated Casualness




There’s a specific breed of celebrity style, one that’s taken root in the scorched earth of Los Angeles paparazzi shots and Instagram grids. It whispers, “Oh this old thing?” while simultaneously screaming, “Look at me, I spent $2,000 on this t-shirt.” It’s a carefully curated nonchalance, a studied effortlessness, and no one does it better than Kendall Jenner and her ilk.


I remember a time when “off-duty model style” meant just that: off-duty. Think ripped jeans and a band tee, hair scraped back in a messy bun, a cigarette dangling from lips slicked with Carmex. It was the antithesis of the glamour they embodied on the runway, a raw, almost defiant rejection of the polish and perfection demanded of them.


But somewhere along the line, something shifted. Perhaps it was the rise of social media, the insatiable need to document and be seen. Or maybe it was the ever-blurring lines between celebrity and influencer, where every sidewalk stroll became a potential photo op. Whatever the catalyst, “off-duty” morphed into a performance of its own, a carefully crafted illusion of spontaneity.


Take Kendall, for instance. She’s a master of the art. A vintage band tee (sourced, no doubt, by a stylist with an encyclopedic knowledge of obscure 70s rock bands) paired with perfectly distressed denim, cinched at the waist with a designer belt that probably costs more than my rent. Her hair is artfully tousled, makeup minimal but flawlessly applied. It’s an image that screams “cool girl,” effortlessly chic, relatable even. But let’s not kid ourselves. This is calculated casualness at its finest.


And it’s not just Kendall. The entire Jenner-Hadid-Bieber axis operates within this aesthetic. Hailey Bieber, a self-proclaimed “vintage enthusiast,” has built an entire brand on this studied nonchalance. Oversized leather jackets, chunky gold jewelry, and a never-ending rotation of sneakers that would make any hypebeast weep. It’s aspirational, yes, but also undeniably out of reach for the average person.


Which begs the question: is there something inherently disingenuous about this calculated casualness? Are these women simply perpetuating unrealistic beauty standards, albeit ones disguised as effortless cool? It’s a valid critique. After all, the very foundation of this aesthetic is built on privilege. The privilege of having access to the best stylists, the most exclusive vintage stores, and a lifestyle that allows for endless paparazzi shots outside trendy cafes.


But there’s also an undeniable allure to it. This carefully curated nonchalance taps into our desire for authenticity, for a break from the overly polished, filtered images that dominate our feeds. It’s a fantasy, yes, but a seductive one nonetheless.


And perhaps that’s the point. Fashion, at its core, is a form of escapism. It allows us to inhabit different personas, to project an image of ourselves that we might not necessarily embody in our everyday lives. And in a world saturated with images, where the lines between reality and performance are increasingly blurred, maybe a little calculated casualness is just what we need. Even if it is all smoke and mirrors.


I’ve seen this play out firsthand, witnessed the evolution of street style from genuine snapshots of personal style to carefully orchestrated photoshoots. And while a part of me mourns the loss of true spontaneity, I can’t help but admire the sheer artistry of it all. The way these women can transform a simple pair of jeans and a t-shirt into a statement, a carefully constructed narrative of who they are (or at least, who they want us to believe they are).


So, is it calculated? Absolutely. Is it contrived? Without a doubt. But is it also incredibly effective? Undeniably so. And in the end, isn’t that the mark of true style mastery? The ability to create an illusion so convincing, so effortlessly cool, that we’re all willing to buy into it, even just for a moment?

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