Vanity Fair’s 2019 Best Dressed List: Celebrating Iconic Celebrity Style and Enduring Fashion Influence
Every September, the fashion world holds its breath as Vanity Fair unveils its highly anticipated annual Best Dressed List. This isn’t just any celebrity roundup; it’s a meticulously curated roster of individuals whose sartorial choices have not only captivated audiences but also pushed the boundaries of contemporary style. Making this ultra-exclusive list is considered a significant achievement, a testament to one’s influence and consistent commitment to fashion excellence. The rigorous selection process, overseen by VF‘s discerning editors, ensures that only the truly deserving earn a spot. The 2019 edition celebrated an eclectic mix of Hollywood’s brightest stars and global icons, from burgeoning style queens to enduring legends, both women and men who effortlessly command attention on red carpets and city streets alike.
Among the celebrated women gracing the list this year were the perpetually chic Jennifer Lopez, 50, Instagram style sensation Zendaya, 23, and the exotically beautiful Priyanka Chopra, 37. These ladies, each a fashion force in her own right, demonstrate a diverse spectrum of style, from timeless elegance to daring avant-garde. Not to be outshone, Hollywood’s dapperly dressed men also secured their place, with Jason Momoa, 39, Harry Styles, 25, and Rami Malek, 38, earning well-deserved recognition for their distinctive fashion statements.
The Women Who Define Modern Glamour and Individuality
The 2019 Best Dressed List showcased an incredible array of female talent, each bringing their unique flair to the global fashion stage. From audacious red-carpet gowns to impeccably curated street style, these women proved that fashion is not merely about clothing, but a powerful form of self-expression.
Zendaya: A Style Chameleon’s Ascent
Zendaya’s inclusion on the list was met with widespread acclaim, solidifying her status as a bona fide fashion icon. Kimberly Drew, a committee member for Vanity Fair‘s Best Dressed List, eloquently captured her impact, stating, “Zendaya blows the roof off how we imagine young stars dress.” This sentiment perfectly encapsulates Zendaya’s fearless approach to fashion, often working in close collaboration with her renowned stylist, Law Roach, to craft looks that are consistently groundbreaking. Her appearance in a magnificent orange-and-pink ostrich feather Marc Jacobs creation for the launch of jewelry brand Âme last December was a prime example of her evolved and mature aesthetic. This wasn’t just a dress; it was a statement of confidence and artistic vision. The ensemble highlighted her ability to carry off high fashion with an innate grace and control over her image. At HollywoodLife, we’ve long admired Zendaya’s impeccable style, from her charming black and white polka dot dress worn for her fragrance launch to her incredibly chic tuxedo-inspired crop top that turned heads during Paris Fashion Week in July. Her fashion journey from Disney star to a global style trailblazer is a masterclass in strategic and authentic image cultivation, demonstrating an unparalleled versatility that allows her to pivot effortlessly between avant-garde couture and effortlessly cool street style.
Jennifer Lopez: Decades of Dazzling Fashion
Jennifer Lopez, a perennial favorite of the magazine, has graced Vanity Fair‘s pages numerous times since her first cover in June 2001. Her inclusion on the Best Dressed List underscores her enduring influence as a fashionista whose style continues to evolve and inspire. For decades, J.Lo has been making headlines with her bold and glamorous fashion choices. Who could forget the iconic plunging green Versace dress she famously wore to the Grammys in 2000? That moment not only cemented her status as a style provocateur but also famously led to the creation of Google Image Search. Two decades later, she continues to deliver one fabulous look after another, whether it’s on a red carpet, during a dazzling stage performance, or simply navigating the streets of New York. Her style is characterized by a blend of confident sensuality, high-octane glamour, and an undeniable ability to make any outfit her own. Lopez’s knack for selecting ensembles that highlight her athletic physique and vibrant personality has made her a consistent trendsetter, proving that true style is timeless and boundless.
Priyanka Chopra: Global Icon with a Unique Sartorial Sense
Priyanka Chopra’s presence on this year’s list was a testament to her increasingly sophisticated and globally-minded style. Her New York City street style, in particular, has been a major talking point, showcasing her ability to blend high fashion with everyday chic. In her interview, Chopra candidly revealed sunglasses as her most “overused” accessory, a small detail that speaks volumes about her approach to accessorizing and adding a touch of cool to any look. She also cited kitten heels as her latest obsession, a practical yet stylish choice that perhaps allows her to maintain a comfortable height dynamic with her husband, Nick Jonas (Priyanka is 5’5″ and Nick is 5’6″). When discussing her dressing philosophy, Chopra admitted, “I don’t think there is such a thing as badly dressed. I’m a moody dresser. So if by ‘badly’ you mean sweats, then at home and on set.” This statement highlights her authentic and adaptable approach to fashion, understanding that style is not about perfection but about comfort, mood, and context. Her ability to seamlessly transition between elaborate red-carpet gowns, elegant traditional Indian attire, and casual-chic street ensembles makes her a true style chameleon with a global perspective.
Other Iconic Women on the List: Diverse Expressions of Style
The 2019 list further celebrated an array of women known for their distinct and influential fashion sensibilities. Zoë Kravitz, 30, with her effortlessly cool and edgy aesthetic, alongside her mother, Lisa Bonet, 51, who embodies bohemian chic and timeless grace, offered a beautiful generational juxtaposition. Their shared yet individualistic approaches to style highlight fashion as a deeply personal and often inherited trait. Also making the cut were the ever-independent and stylish Chloë Sevigny, 44, known for her unique indie sensibility and trendsetting street style, and the incomparable Celine Dion, 51, whose recent high-fashion renaissance has captured the hearts of critics and fans alike. Dion’s transformation into a true fashion icon, embracing avant-garde couture with fearless enthusiasm, was one of the most exciting narratives of the year, proving that age is truly just a number when it comes to style.
The Men Redefining Red Carpet Style and Masculinity
The Best Dressed List wasn’t exclusively for the ladies; the men featured in 2019 demonstrated that masculine style can be just as diverse, bold, and influential. These gentlemen are breaking traditional molds and inspiring a new generation with their daring choices.
Jason Momoa: Breaking Barriers with Bold Choices
Representing the men with a distinct and memorable flair, Lisa Bonet’s handsome husband (and Zoë’s stepdad!), Jason Momoa, 40, earned his inaugural spot on the list. Momoa has been consistently turning heads with his unique approach to red carpet dressing, making “blush” his signature shade. His memorable appearance at the Oscars earlier this year in a suave pink velvet suit by Fendi was a pivotal moment. The story behind this iconic suit adds another layer of charm: it was inspired by a velvet scrunchie gifted to him by one of his makeup artists. This personal touch speaks volumes about his authentic and playful approach to fashion. Adding to its significance, the Fendi suit was one of legendary designer Karl Lagerfeld’s final creations before his passing in February, lending it a poignant historical weight. Momoa’s style is a fascinating blend of rugged masculinity and unexpected elegance, challenging conventional notions of menswear with his embrace of color, texture, and custom tailoring. His presence on the list celebrates a new era where men’s fashion is becoming increasingly expressive and less confined by traditional norms.
Harry Styles: The Apex of Androgynous Chic
Also earning a spot was Harry Styles, whose fashion choices have consistently pushed boundaries and redefined modern masculinity. Styles is a pioneer of gender-fluid fashion, frequently blurring lines between traditionally male and female clothing with effortless confidence. His collaborations with Gucci’s Alessandro Michele have produced some of the most memorable and influential looks of recent years, from ornate suits to sheer blouses and pearl necklaces. Styles’ stage presence is inseparable from his sartorial statements, using fashion as a dynamic extension of his artistic expression. His inclusion on the Best Dressed List signifies a broader cultural shift towards more inclusive and adventurous menswear, where self-expression and individuality take precedence over rigid gender conventions. He’s not just wearing clothes; he’s crafting a narrative of freedom and daring in fashion that resonates deeply with his vast fanbase.
Rami Malek: Mastering Classic Sophistication
Rami Malek, known for his compelling performances, also garnered recognition for his impeccably tailored and sophisticated style. Malek embodies a return to classic Hollywood glamour, often seen in perfectly fitted suits and tuxedos that exude an old-school charm with a modern edge. His post-Oscar winning style, in particular, demonstrated a consistency in sharp, clean lines and a preference for timeless elegance over fleeting trends. He has a keen eye for detail, often opting for subtle variations in fabric, cut, and accessories that elevate his formal wear beyond the ordinary. Malek’s fashion choices convey a sense of understated confidence and refined taste, proving that classic doesn’t have to mean boring, but rather a foundation for enduring style.
Esteemed Gentlemen: Brad Pitt and Keanu Reeves
The list further highlighted the understated yet powerful style of Hollywood veterans like Brad Pitt and Keanu Reeves. Pitt, known for his relaxed yet effortlessly cool aesthetic, often favors well-cut casual wear and an easy-going elegance that belies his superstar status. His style is a masterclass in approachable sophistication, proving that impactful fashion doesn’t always require elaborate ensembles. Keanu Reeves, on the other hand, embodies an enduring appeal with his signature, often monochromatic, simple yet powerful looks. His fashion is characterized by practicality, comfort, and a subtle rebel edge, making him a unique and respected figure in the style landscape. Both Pitt and Reeves demonstrate that true style is often about authenticity and comfort in one’s own skin, rather than strictly following trends.
Beyond the Looks: The Impact of the Best Dressed List
The Vanity Fair Best Dressed List is more than just a roll call of fashionable celebrities; it’s a cultural barometer that reflects the ever-evolving landscape of fashion, influence, and personal branding. The 2019 list underscored several key shifts in the industry. It highlighted the increasing importance of stylists as key architects behind celebrity images, transforming actors and musicians into global style icons. It also celebrated the blurring lines between high fashion and street style, recognizing that impactful fashion moments can occur anywhere, not just on the red carpet. Furthermore, the list’s growing diversity, both in terms of age and background, reflects a more inclusive vision of beauty and style that resonates with a wider audience. The rise of social media platforms, particularly Instagram, has also amplified the reach and immediate impact of these fashion choices, turning individual celebrity looks into global trends overnight.
Conclusion: A Legacy of Style and Influence
The 2019 Vanity Fair Best Dressed List served as a powerful reminder of fashion’s capacity to inspire, provoke, and define culture. From Zendaya’s daring couture experiments to Jennifer Lopez’s enduring glamour, and from Jason Momoa’s boundary-pushing menswear to Harry Styles’ gender-fluid statements, each honoree contributed to a rich tapestry of contemporary style. These individuals aren’t just wearing designer clothes; they are embodying confidence, creativity, and a fearless spirit that transcends fleeting trends. Their inclusion on this esteemed list solidifies their status as true fashion icons, leaving an indelible mark on the industry and inspiring countless others to embrace their own unique sartorial voices for years to come.