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Arts & Culture
01 January 2026

Chappell Roan Redefines Fashion With Daring 2025 Looks

The Grammy-winning singer celebrates her boldest styles of the year while challenging the fashion world’s obsession with exclusivity and high price tags.

Chappell Roan, the rising pop sensation and recent Grammy winner, has never shied away from bold self-expression—especially when it comes to fashion. As 2025 draws to a close, Roan took to Instagram on December 29 to share her “personal Top 10 Looks Of 2025,” giving fans and fashion enthusiasts a whirlwind tour through a year filled with daring style choices, heartfelt gratitude, and a fresh philosophy on what it means to be fashionable today.

Roan’s number one pick? The vintage Jean Paul Gaultier 2003 couture gown she wore to the 2025 Grammy Awards in February. According to Harper’s Bazaar, the gown was a showstopper: a dreamy cascade of yellow and pale blue tulle, adorned with an illustration of Edgar Degas’ iconic painting, “Dancer With a Bouquet.” The visual impact was immediate, cementing Roan’s place among the year’s most memorable red carpet moments and earning her widespread acclaim from both fans and critics alike.

But Roan’s sartorial journey in 2025 was hardly limited to just one dazzling dress. Her Instagram roundup, as reported by ABC Audio, revealed a parade of standout ensembles that showcased her eclectic tastes and fearless approach. The number two spot went to the sultry red two-piece outfit she rocked at the U.K.’s Reading Festival, a look that radiated confidence and energy. The third place was reserved for a Valentino gown she wore during Paris Fashion Week, further proving her ability to turn heads on international runways and stages alike.

Other highlights from her top ten included the Rapunzel-like hair she donned in “The Subway” music video, the “Private Inspector” look from the video for “The Giver,” a hot pink disco-inspired ensemble for her Met Gala debut, and the outfit she wore onstage to accept the Best New Artist trophy at the Grammys. Each look, distinct in its own right, contributed to a narrative of experimentation and unapologetic individuality that has become Roan’s trademark.

Reflecting on the year, Roan expressed heartfelt appreciation for the creative minds and skilled hands who helped bring her visions to life. She singled out designers like Genesis Webb and the many seamstresses who, in her words, “put many hours into my custom looks.” In a candid Instagram caption, she wrote, “Just my opinion u don’t have to agree !!! I love dressing up obvs & this year I got to wear things I’ve only dreamed of. Thank you to all the houses that dressed me this year and all the seamstress fairies who put many hours into my custom looks. Mwahhh I feel so princess!!! Xoxox.”

Yet, for all the glitz and glamour, Roan’s message went beyond mere aesthetics. She used her platform to challenge the longstanding notion that fashion is an exclusive club reserved for those with access to high-end couture and exorbitantly priced garments. In her own words, “I don’t believe you need to wear high end couture or insanely expensive clothing to be considered fashionable or ‘in the fashion circle’ f--- that s---. That is weird and lame and very OUT in my opinion.” Her blunt rejection of gatekeeping resonated with many, as she continued, “Gate keeping is stupid. Let’s all just be cute together.”

Roan’s philosophy is rooted in authenticity and inclusivity—a refreshing stance in an industry often criticized for its elitism. As she put it, “I think looking cool is like… being you and being different and trying new things. Chic is fun but fun is funner … F--- it be weird and bold otherwise who cares??” This rallying cry for self-expression over conformity has struck a chord with her followers, sparking conversations about the evolving definition of style in the digital age.

According to Harper’s Bazaar, Roan also made a point to emphasize that the real “cool” factor comes from authenticity, not price tags or designer labels. “I don’t believe you need to wear high end couture or insanely expensive clothing to be considered fashionable or ‘in the fashion circle’ f--- that s---. That is weird and lame and very OUT in my opinion,” she reiterated. Her words, both playful and pointed, captured a broader sentiment within the fashion community: that creativity and individuality matter far more than status or wealth.

Throughout 2025, Roan’s style choices have consistently pushed boundaries, blending elements of fantasy, nostalgia, and modernity. Her Met Gala debut, for example, saw her sporting a hot pink disco-inspired outfit that paid homage to the exuberance of past eras while feeling entirely of the moment. At the Reading Festival, her red two-piece ensemble exuded a sense of power and playfulness, while her Paris Fashion Week appearance in Valentino demonstrated her ability to glide seamlessly between avant-garde and classic sophistication.

But perhaps what sets Roan apart most is her willingness to use her platform to advocate for a more inclusive and accessible vision of fashion. By thanking the “seamstress fairies” and openly discussing the collaborative nature of her wardrobe, she highlights the often-overlooked craftspeople behind the scenes. Her gratitude extends beyond designers to the many hands that contribute to each look, reminding fans that style is a team effort and that magic happens when creativity is shared.

Her approach to fashion isn’t just about personal taste—it’s a broader statement about the power of self-expression. By encouraging her fans to “be weird and bold otherwise who cares??” Roan invites a new generation to embrace their quirks and experiment without fear of judgment. In an era where social media can sometimes feel like a battleground of curated perfection, her message of authenticity feels especially timely.

If there’s one takeaway from Chappell Roan’s year in fashion, it’s that true style transcends trends and price tags. Whether she’s channeling a Degas ballerina on the Grammy red carpet, dazzling in Valentino at Paris Fashion Week, or simply playing dress-up for the sheer joy of it, Roan proves that the most memorable looks are those that tell a story—one of creativity, collaboration, and the courage to stand out.

As 2025 comes to a close, Roan’s vibrant, unapologetic approach offers a refreshing reminder: fashion is, at its heart, about having fun and being yourself. And as she so aptly put it, “Chic is fun but fun is funner.”