Kylie Jenner: A Decade of Red Carpet Dressing

Kylie Jenner has been turning heads this awards season with thoughtful, bold fashion choices that feel deeply personal but unmistakably high-fashion. At the Los Angeles premiere of The Moment, marking her acting debut, she wore a sculptural Maison Margiela Spring/Summer 2026 look, a ruffled halter crop top paired with a low-slung black maxi skirt that exposed her toned midriff. The outfit was a clear reinvention of a runway piece adapted for the red carpet, showing Jenner’s comfort with pushing silhouettes while staying rooted in couture heritage

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Just weeks earlier at the 2026 Golden Globes, she stepped onto the carpet in a custom gold gown by Ashi Studio. The design featured crystal-encrusted straps and over-the-top sparkle, complementing her diamond jewellery, dramatic, glamorous, and perfectly suited to the star-studded event. 

These recent looks underscore a shift: Jenner now embraces red carpet dressing with a sense of maturity and confidence that doesn’t rely on shock value alone.

The Early Years

Jenner’s earliest fashion moments were tied to youth-centric trends, streetwear influences, and the early Kardashian-Jenner style world of logo mania and body-con silhouettes. Her red carpet style in the early 2010s was often about standing out — think bold colours, curve-hugging gowns, and an embrace of high glam that was full of personality.

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A notable turning point came in 2017 when she wore Versace to the Met Gala with a platinum blonde wig and plenty of fringe. That moment signalled a willingness to lean into themed dressing rather than just walk the carpet.

Most Memorable Gala and Event Looks

As Jenner’s celebrity continued to grow, so did her red carpet choices. At the 2025 BAFTAs, she proved her refined taste by wearing a vintage John Galliano gown — a striking black backless piece adorned with sequined petals that felt timeless yet elevated.

At various year-end and film festival parties, she’s shown versatility: a custom Miu Miu beaded dress at the Oscars ceremony and a daring Ashi Studio couture corset gown at the Vanity Fair Oscar party. 

These aren’t just outfits. They’re strategic plays in how she positions herself as both a fashion figure and a partner to one of Hollywood’s buzziest actors.

Met Gala Moments That Stole the Show

Jenner’s Met Gala fashion chronology reads like a hit list of festival-level red carpet moments. In 2016, she debuted in a futuristic Balmain gown for the Manus x Machina theme — a heavily embellished look that showed she could stand with fashion’s young stars. 

Her 2019 Camp look in a lavender Versace ensemble, complete with feathered sleeves and a matching wig, became one of the most talked-about outfits of that year. 

In 2022, she paid tribute to the late Virgil Abloh with a custom Off-White bridal gown, paired with a baseball cap and tiny veil—an unexpected twist that blurred fashion rules. 

At the 2024 Gala, she embodied the theme by wearing a garden statue-inspired custom Oscar de la Renta gown with a dramatic trumpet skirt and sculptural bodice. 

Most recently, in 2025, she turned to tailoring with a custom Ferragamo gown featuring corseted bodice proportions and sleek gloves that balanced sensuality and structure. 

Award Show Excellence and Designer Collaborations

Jenner’s award-show rotation reads like a who's who of fashion houses. She’s tapped Margiela, Ashi Studio, John Galliano, Miu Miu, and vintage Versace for major nights, proving she’s comfortable both with archival treasures and bespoke couture.

One of her strongest collaborative moments came at the 2026 Critics' Choice Awards, where she chose a restored Gianni Versace couture gown from Tab Vintage that felt simultaneously classic and contemporary. 

Her stylists—sisters Mackenzie and Alexandra Grandquist—have become key creative partners in shaping her evolving red carpet language.

Casual Kylie Jenner Outfits That Went Viral

Her street style might not always make headlines like her gowns, but she’s cultivated moments of relaxed cool: think oversized outerwear with sleek accessories, high-fashion sportswear paired with minimalist basics, and boots that feel equally editorial and wearable.

Her presence off-duty—whether courtside or during fashion week street sightings—has shown a growing ease in translating trends into everyday outfits that still feel personal.

The Glam completing the Kylie Jenner Look

Her makeup and hair are as iconic as her clothes. Sleek up-dos, glossy blowouts, dramatic eyes, and bold lips are recurring motifs in her beauty toolkit. Over the years, her glam artists have helped her shift from ultra-groomed late-2010s gloss to more refined, editorial lines that elevate any look. The result is a signature finish that feels polished and intentional without ever looking static.

Kylie Jenner’s style arc shows real evolution: she started with bigger moments, then learned how to make every appearance count—whether it’s a couture gown at a premiere, a themed Met Gala outfit, or a vintage archive find that turns heads. Her recent awards-season fashion has been some of the strongest yet, suggesting she’s entering a phase where she measures impact with nuance, depth, and a clear fashion identity that feels hers uniquely.

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