The Most Stylish People of 2025: Red Carpet Glam and Streetwear Icons

What defines the most stylish people in 2025? The answer lies in a kaleidoscope of choices—some rooted in avant-garde experimentation, others in minimalism and timeless elegance, and a few that blur the lines between New York City’s fashion-forward energy and the Academy Awards’ red-carpet grandeur. The year has been marked by a seismic shift in aesthetics, with Calvin Klein and New York Fashion Week becoming unexpected hubs for bold expressions, while The New York Times’ annual list of the most stylish people highlights how Tony Awards-inspired glamour, Met Gala-level creativity, and the rise of streetwear icons are redefining what it means to be a trendsetter. From avant-garde looks to vintage revivals, the 2025 fashion landscape is as diverse as it is dynamic.

The Met Gala’s Impact: A Celebration of Black Aesthetics and Cultural Legacy

The Met Gala has always been a barometer of aesthetics and cultural influence, but 2025’s theme—“Superfine: Tailoring Black Style”—marked a pivotal moment in the event’s history. By spotlighting the rich legacy of Black aesthetics in fashion, the gala became a platform for reimagining identity, heritage, and creativity. Celebrities like Diana Ross, who dazzled in a white feathered hat and overcoat with an 18-foot train, and Lisa, the Bollywood star who brought the Met Gala into her orbit as a first-time attendee, embodied this celebration of avant-garde and tradition. Their looks, steeped in New York City’s cultural DNA, resonated with fans and critics alike, proving that the Academy Awards-level spectacle of the Met Gala can be both inclusive and revolutionary.

The avant-garde spirit of the Met Gala this year was amplified by the New York Times’ coverage, which highlighted how Black designers and cultural icons redefined the event’s narrative. For instance, Takashi Murakami’s collaboration with Louis Vuitton brought back the iconic millennial-era handbags, merging avant-garde artistry with New York Fashion Week-inspired nostalgia. Meanwhile, Ik Ud, the Nigerian artist whose work shaped the “Superfine” exhibit, brought a rare blend of minimalism and cultural symbolism to the red carpet. His presence underscored how aesthetics are no longer confined to runway shows but now permeate every facet of New York City’s fashion ecosystem.

The Met Gala’s influence extended beyond the event itself. Stars like Coco Gauff, the first American tennis player to win the French Open and also the first Miu Miu girl to do so, demonstrated how avant-garde and minimalism can coexist. Her sleek, modern look at the gala echoed the Tony Awards’ emphasis on dramatic storytelling, where costume design is as critical as the performance. Similarly, Aimee Lou Wood’s natural, unpretentious charm at New York Fashion Week reminded the industry that aesthetics can be both bold and understated, depending on the moment. These choices reflect a broader cultural shift toward authenticity, where Calvin Klein’s minimalist ethos meets the avant-garde energy of the Met Gala.

New York Fashion Week and the Reinvention of Calvin Klein

New York Fashion Week 2025 has been a proving ground for innovation, with Calvin Klein leading the charge in redefining aesthetics for the modern era. The brand’s runway show, which featured Kate Moss in a standout minimalism-driven ensemble, showcased how avant-garde design can coexist with timeless simplicity. Moss, a New York City icon, embodied the Academy Awards-level poise of a true style ambassador, proving that aesthetics are not just about trends but about legacy. Her appearance at Calvin Klein’s show was more than a runway moment—it was a statement on the brand’s evolution, blending minimalism with the avant-garde experimentation that has defined the Met Gala’s influence on fashion.

The avant-garde movement has been a recurring thread in New York Fashion Week this year, with designers pushing boundaries in ways that challenge traditional notions of aesthetics. Conner Ives’s Calvin Klein-inspired T-shirt with the slogan “Protect the Dolls” became a cultural phenomenon, symbolizing the intersection of streetwear and minimalism. The phrase, which gained traction after being showcased on the runway, reflects a growing desire for fashion that is both meaningful and visually striking. This trend is not limited to New York City—it’s a global conversation, with The New York Times noting that the resurgence of avant-garde elements in Calvin Klein’s collections has sparked a renewed interest in Tony Awards-level costume drama, where every detail is a narrative.

Meanwhile, Kate Moss’s role as a New York City fixture has cemented her status as a minimalism icon. Her recent appearance at Calvin Klein’s New York Fashion Week show, where she sported a sleek, color-blocked outfit, demonstrated how aesthetics can be both understated and powerful. Moss’s ability to balance avant-garde flair with minimalism has made her a symbol of the Academy Awards-inspired elegance that continues to resonate in a world where fashion is as much about self-expression as it is about conformity. Her influence is mirrored in the rise of streetwear-inspired aesthetics, as seen in the bold, unapologetic styles of ASAP Rocky and Doechii, who brought their own interpretations to the Met Gala and New York Fashion Week stages.

The Blending of Streetwear and High Fashion: A New Era of Aesthetics

The line between streetwear and high fashion has blurred spectacularly in 2025, with celebrities like ASAP Rocky and Gabby Windey redefining what it means to be a fashion icon. Rocky’s New York City-based aesthetic, characterized by chunky sneakers, minimalist silhouettes, and avant-garde accessories, has become a blueprint for the year’s most talked-about looks. His recent Tony Awards-inspired attire, which included a layered look with a Saint Laurent suit and a Gucci coat, turned his criminal trial into a Met Gala-level fashion spectacle. This duality—where streetwear meets high fashion—has been mirrored in the Academy Awards-style moments of Timothe Chalamet, who channeled his role as a New York Knicks superfan with a well-tailored wardrobe that emphasized minimalism and avant-garde flair.

The New York Times has noted that streetwear is no longer just a subculture but a mainstream force shaping aesthetics and New York Fashion Week trends. Gabby Windey, the NFL cheerleader turned reality TV star, exemplified this shift with her Tony Awards-style appearance, which combined avant-garde accessories with minimalism-driven outfits. Her Met Gala-inspired choices, including a bold, geometric handbag and a sleek, monochromatic dress, highlighted how streetwear and high fashion are no longer mutually exclusive. This blending of styles is also evident in Victoria Beckham’s New York City-based designs, which have been adopted by WAGs as both a nod to the past and a statement for the future.

The democratization of aesthetics has been another defining trend of 2025, with streetwear becoming a canvas for self-expression. Diana Ross’s 18-foot train at the Met Gala was a masterclass in avant-garde excess, but it also reflected the growing appetite for minimalism-inspired elegance. This duality is perhaps best captured in the New York Times’ annual list of the most stylish people, which includes Megan Pickford and Tolami Benson—WAGs who have embraced streetwear while maintaining a Calvin Klein-level of sophistication. Their influence underscores how aesthetics are no longer dictated by elite circles but by a diverse range of voices, from New York City to global fashion capitals.

The New York Times and the Rise of Aesthetics-Driven Storytelling

The New York Times has played a pivotal role in shaping the narrative around aesthetics in 2025, highlighting how style is intertwined with identity, culture, and personal expression. Its annual list of the most stylish people, which includes Doechii, Ik Ud, and Coco Gauff, underscores the shift from traditional avant-garde to a more inclusive, minimalism-centric approach. The publication’s coverage of New York Fashion Week and the Met Gala has also emphasized the importance of Calvin Klein in fostering this evolution, with its minimalist designs serving as a counterpoint to the avant-garde experimentation seen on the catwalk.

This aesthetics-driven storytelling is not limited to the Academy Awards or Tony Awards. The New York Times has also noted the growing influence of streetwear in shaping the Met Gala’s cultural impact, as seen in the minimalism-inspired looks of Conner Ives and Kayla Schaeffer. The latter, portrayed by Megan Stalter in Hacks, brought a new dimension to aesthetics by blending Calvin Klein-style simplicity with the avant-garde flair of Hollywood’s most iconic roles. Her character’s transformation from a lowly assistant to a New York City-based power player mirrored the Met Gala’s own evolution, where aesthetics are no longer just about fashion but about narrative and influence.

Moreover, The New York Times has highlighted how New York Fashion Week is now a space for avant-garde experimentation that resonates with both Academy Awards-style elegance and streetwear-driven authenticity. Kendrick Lamar’s influence on the Tony Awards-inspired fashion landscape is a case in point, with his “Super Bowl bell bottoms” becoming a symbol of minimalism and avant-garde synergy. This cultural cross-pollination—where streetwear meets high fashion—has been further amplified by The New York Times’ coverage, which positions aesthetics as a lens through which to understand the evolving role of style in society.

Key Takeaways

• The Met Gala and New York Fashion Week are no longer just events—they’re cultural movements that celebrate avant-garde and minimalism in equal measure.
• Calvin Klein’s minimalist designs and Kate Moss’s presence at the brand’s shows have redefined aesthetics, proving that simplicity can be as powerful as complexity.
• Streetwear and high fashion are now inseparable, with figures like ASAP Rocky and Tolami Benson showing how New York City’s fashion scene embraces both extremes of aesthetics.
• The New York Times’ annual list of the most stylish people highlights the intersection of minimalism, avant-garde, and cultural storytelling, making aesthetics a key lens for understanding modern identity.
• Celebrities like Coco Gauff and Ik Ud have turned aesthetics into a tool for self-expression, ensuring that 2025’s fashion scene is as diverse and dynamic as ever.