Like all celebrities who are fun to watch (no, I’m not about to wade into that who’s-more-interesting-to-look-at drama), Kendall Jenner’s style journey didn’t follow a clear path. Not all that long ago, she was the typical SoCal girl: denim cut-offs, crop tops, and an obligatory flower crown. It was all very Coachella, which also happens to be where she launched herself as a fashion darling. It’s easy to look back with smug disdain at the body gems and cliché boho trappings, but at the time, these were the looks that first landed her on the best-dressed lists.
Somewhere along the way, things shifted. Kendall’s fashion journey might’ve been a slow burn, but what began with an upbeat, carefree pop morphed into something richer (literally), more introspective, and definitely cooler. Here’s how her style has transformed from Calabasas girl-next-door to runway royalty.
Coachella Kendall
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As I’ve mentioned, in the early 2010s, Kendall Jenner’s laid-back wardrobe was emblematic of her California upbringing — all easy, breezy SoCal in the form of fringed jackets paired with denim shorts and gladiator sandals, Converse, or ankle boots. Not exactly groundbreaking stuff, but because she looks good wearing just about anything, she quickly started climbing the fashion ranks. And credit given: she does have an innate ability to elevate even the most basic of pieces.
The Rise of the Off-Duty Model
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When Kendall’s modelling career started taking off in the mid-2010s, her style shifted towards a more fashion-forward approach. Pretty soon, she’d become the blueprint for the model-off-duty look: tailored blazers thrown over slouchy tees, oversized coats that engulfed her diminutive frame. She’d still mix them with the same trainers most girls her age were wearing, often Converse, and this balancing act gave her a relatability that made her ripe for those early social media “get the look” posts.
This was a high point for street style, and Kendall, with her mix of high-end and casual pieces, slotted in perfectly. Blazers, oversized outerwear, wide-leg trousers, graphic tees, trainers, and casual accessories became the cornerstone of her wardrobe.
A key moment came in 2015 when she wore an ice-white wrap top and cigarette pants with a pair of pewter brogues after closing the Chanel show at Paris Fashion Week. The look was modern and fuss-free and would come to sum up her attitude towards dressing.
Kendall at The Met
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As Kendall’s star continued to soar, so did her sartorial experimentation. She transitioned from being a street style star to a red carpet fixture, stepping out in exquisite haute couture creations. Her Met Gala appearances — she’s been almost every year since 2014 — became an annual highlight, showcasing her shift towards an increasingly polished, couture-focused wardrobe. Her 2014 Met debut was safe, the kind of gown you can imagine the cast of Gossip Girl clad in. Actually, the custom Topshop gown, with its structured bodice, fishtail hem and champagne silk fabrication, wasn’t far off Serena’s Cotillion dress.
2017’s naked gown marked another turning point still. The dress, from La Perla’s Haute Couture collection, showed a shift away from the safer, red carpet fare of previous years towards a more directional aesthetic. The chain-mail–style gown draped over her like liquid metal, while the plunging open back revealed a web of glinting, metallic mesh. Ditching 2014’s bouncy blow dry, her hair was styled in a soft, voluminous wave pushed away from her face, giving the whole look that effortless, slightly undone glamour.
A sartorial spectacle was well underway by 2019 when Kendall, twinning with Kylie, turned up in a scorching orange gown dripping in beads and framed by a halo of feather plumage. The look was Versace, but it called to mind Cher’s (also at the Met Gala) Bob Mackie-designed catsuit. Full fashion theatrics.
Today’s Luxe Minimalism
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Today, Kendall’s style has evolved into an embodiment of luxurious minimalism. She has found her sartorial sweet spot in pared-back, timeless pieces that reflect an elevated, understated approach to fashion. Gone are the days of experimenting with bold prints or eclectic styles; in their place, Kendall has embraced clean lines, muted palettes, and perfectly tailored garments that exude sophistication without excess.
Her modern-day wardrobe favours the kind of quiet luxury that has become synonymous with the likes of The Row, Celine, and Givenchy: brands whose ethos revolves around understated elegance and craftsmanship. Whether she’s wearing an oversized trench, a sharp blazer, or a sleek black slip dress, her aesthetic revolves around pieces that transcend trends, focusing instead on enduring style.
Her Instagram, often a mood board for minimalist luxury, is stacked with looks that marry high fashion with do-to-day practicality. The art of quiet sophistication has been mastered via fluid silhouettes, luxurious neutrals, and structured outerwear that require little to no embellishment to stand out. This new phase in her style is a far cry from the bold statements of her earlier days, but it proves just how versatile her fashion journey has been.