The Two Daring Golden Globes Looks That Defined Kylie Jenner’s Awards Show Era
Kylie Jenner’s presence at the Golden Globe Awards has become a major cultural moment, not for her own nominations, but for her high-profile appearances as the date of actor Timothée Chalamet, and the dramatic, vintage fashion choices she has made. Unlike her sisters who often walk the red carpet, Jenner has twice opted for a more low-key entrance, yet her outfits—particularly the latest one from the 2025 ceremony—have sparked massive online buzz and even a behind-the-scenes drama documented on her reality show. The contrast between her coordinating, romantic 2024 debut and the revealing, controversial 2025 look shows a clear evolution in her awards show style.
As of late December 2025, the conversation surrounding Kylie Jenner's second Golden Globes appearance remains front and center, especially after revelations from *The Kardashians* detailed her last-minute anxiety over the daring neckline of her vintage gown. Her strategy of skipping the red carpet and making a statement once inside the Beverly Hilton has solidified her status as a power player in the awards show fashion landscape, leveraging rare vintage pieces to create unforgettable, conversation-starting moments alongside her Oscar-nominated boyfriend.
Kylie Jenner: A Brief Biography and Profile
Kylie Kristen Jenner is an American media personality, socialite, and businesswoman. She has leveraged her family's fame into a massive personal brand, primarily through her cosmetics company, Kylie Cosmetics, and her role on the reality television series *Keeping Up with the Kardashians* and its successor, *The Kardashians*. She is one of the most-followed people globally on Instagram and a major figure in contemporary fashion and beauty.
- Full Name: Kylie Kristen Jenner
- Date of Birth: August 10, 1997
- Place of Birth: Los Angeles, California, U.S.
- Parents: Kris Jenner (née Houghton) and Caitlyn Jenner (formerly Bruce Jenner)
- Siblings: Kendall Jenner, Kourtney Kardashian, Kim Kardashian, Khloé Kardashian, and Rob Kardashian
- Children: Stormi Webster and Aire Webster (with Travis Scott)
- Profession: Media Personality, Model, Businesswoman (Kylie Cosmetics, Kylie Skin)
- Relationship Status: Dating Timothée Chalamet (as of 2025)
- Notable Achievements: Youngest self-made billionaire (formerly, according to Forbes), Time's Most Influential Teens, massive social media following.
The 2025 Golden Globes: Vintage Versace, The Wardrobe Malfunction, and The ‘Tits Out’ Drama
Kylie Jenner's 2025 Golden Globes look was arguably her most audacious and talked-about awards show moment to date. Attending to support Timothée Chalamet, who was a nominee for his work in *Dune: Part Two* (or another project), she made a deliberate choice to skip the official red carpet, instead making her grand entrance directly inside the Beverly Hilton ballroom.
A Daring Chainmail Homage
For her second Globes appearance, Jenner chose a spectacular vintage Versace chainmail gown. The dress was a glittering, black and gold number that immediately drew comparisons to an iconic fashion moment of the past: Elizabeth Hurley’s famous 1999 CFDA Fashion Awards look. The gown featured a mix of black silk and lycra, held together by oversized, gold-toned safety pins that created daring cutouts around the waist and bodice. This bold, party-dress aesthetic was a significant departure from the more demure lace she wore the previous year, signaling a more confident and provocative fashion stance.
The Behind-the-Scenes Anxiety and Kris Jenner’s Opinion
What made the 2025 look truly newsworthy was the subsequent revelation on *The Kardashians* reality show. A recent episode captured Kylie’s pre-event anxiety about the revealing nature of the vintage Versace dress. In a candid moment, she reportedly expressed concern to her mother, Kris Jenner, asking if it was "appropriate" to have her "tits out" at such a prestigious event while accompanying Chalamet. This vulnerability humanized the usually guarded star and added a layer of relatable drama to the high-fashion moment. Kris Jenner, the matriarch and manager, likely offered her signature supportive, yet business-minded, advice.
The Wardrobe Malfunction That Went Viral
Adding to the list of talking points, the vintage nature of the gown also led to a minor wardrobe malfunction. Reports suggested the dress was "bursting at the seams" at one point during the evening, a common risk when wearing delicate, decades-old designer pieces. Despite the slight mishap, the overall impact of the vintage Versace look was one of high glamour and a successful channeling of a classic, sexy Hollywood aesthetic, cementing her place in the conversation of the night's best-dressed, or at least, most-talked-about, attendees.
The 2024 Golden Globes Debut: Vintage Lace and Awards Show PDA
Kylie Jenner’s first-ever Golden Globes appearance in 2024 was a landmark moment for her relationship with Timothée Chalamet, as it marked their official debut as a couple at a major awards ceremony. The event instantly made them "awards show official," confirming their highly speculated romance to the world.
A Coordinated, Romantic Look
For this milestone event, Jenner chose a significantly different aesthetic. She wore a sheer, black lace bodycon dress with a low back, a vintage piece by the Japanese-French designer Hanae Mori. The gown was embellished with subtle, shiny black beads and was an elegant, under-the-radar choice that still showcased her figure. The look was part of a subtly coordinating effort with Chalamet, who was nominated for his role in *Wonka*. His all-black, sparkly suit complemented her vintage lace, creating a cohesive and romantic visual narrative for their first public outing on this scale.
The Kiss and Viral Moments
The 2024 Golden Globes was less about the fashion controversy and more about the public display of affection (PDA). Throughout the evening, the couple was captured sharing intimate moments, including several kisses and whispers, which instantly went viral across social media platforms. This affectionate behavior was a clear statement about the seriousness and comfort level of their relationship, shifting the focus from individual celebrity status to their dynamic as a power couple. The Hanae Mori gown, therefore, became synonymous with their "coming out" as a celebrity pair.
The Power of Vintage Fashion and Topical Authority
Kylie Jenner’s repeated choice of vintage gowns—the Hanae Mori in 2024 and the Versace in 2025—is a calculated move that adds significant topical authority and gravitas to her fashion profile. By wearing pieces from legendary designers like Gianni Versace (the original designer of the safety pin concept) and Hanae Mori, she taps into fashion history, elevating her style beyond fast fashion trends. This strategy not only makes her outfits unique and impossible to replicate but also aligns her with a growing celebrity movement toward sustainability and archival fashion, a key trend in high-end style reporting.
The decision to skip the red carpet, a move often associated with A-list actors who prioritize privacy, also adds to her mystique. It allows the focus to shift entirely to the *look* and the *moment* inside the event, rather than the standard red carpet procession. The subsequent revelations on *The Kardashians* further amplify the topical relevance, creating a multi-platform, multi-day media cycle that keeps her Golden Globes appearance trending long after the ceremony ends. Her two appearances have successfully established a new awards show playbook: use rare vintage, bring the drama, and let the PDA do the talking.
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