There are many ways to define “best dressed.” It is subjective and arbitrary and hardly an exact science. And anyway, “best” lists, which lay claims to the “best in the world” for a specific category, are not only preposterous, they are theoretically impossible. Because no one person or organization can possibly say they scoped out the entire world in search of the ultimate candidates.
Undoubtedly, there are many more worthy souls – they just haven’t made movies, paraded on red carpets, found themselves in gossip columns, been subjects of fashion websites, mugged for the paparazzi outside fashion shows, or enlisted the aid of PR mavens to get their mugs photographed here there and everywhere. So it’s all to be taken with a grain of salt.
I always try to steer clear of those who made my past lists because they would invariably be on my new list every year; so I suppose you can consider them to be my “Hall of Famers.” And if I do use them, it’s not in the same way. See our 2018 Best Dressed List.
For my latest installment, I once again focused on diversity and used categories that are relevant and topical. And I wanted to inject an element of surprise. The images used were culled from the past year or two. In random order:
Best Dressed in Trainers: Giovanna Battaglia Engelbert
There’s a time for dressing up, a time for dressing down, and a time to be dressed up and dressed down. Nobody navigates the when, the where, and the how as expertly as a renowned stylist, fashion editor, and author Gio. Her legendary exuberant style remains the same, regardless of whether she is attending fashion shows, special events, evening galas, or relaxing on down time. Gio’s closets brim with the best of everything, and she has a never-ending stockpile of the most glorious shoes on the planet.
She also has a vast cache of trainers and sneakers, both classic and jazzy, which she rotates on a whim. Anybody who thinks athleisure is dead and that sneakers are kaput should take a page from this perennial best-dressed style setter. She is pictured here looking effortlessly chic, comfortable and ready to go. Or in this case, read to Gio!
Best Dressed and Most Powerful: Nancy Pelosi
Nancy Pelosi, the Speaker of the House, is a force to be reckoned with. Mrs. Pelosi’s wardrobe is appropriately authoritative, polished, and pulled together at all times. She is not afraid to stand out in a sea of sensible flats, and quiet suiting on Capitol Hill and at the heart of her chic, fashion personage is a predilection for smart tailoring and her prudent use of accessories.
While the 79-year-old is most known for her strong-shouldered power suits, her fashion icon status was cemented after she was photographed wearing that Max Mara burnt orange funnel neck Fire Coat exiting the White House with Senator Schumer after that now famous meeting with President Trump.
Best Dressed Warrior: Daenerys Targaryen
Even if you were one of those, who thought the season finale of “Game of Thrones” was a disappointment, what cannot be denied is this critically acclaimed award-winning fantasy serial drama has been a visual goldmine since its inception in 2011. Not only because of the expansive locations and amazing special effects but because of the fashions.
No detail was too small for costume designer Michele Clapton, who created the astonishing costumes for the first 5 seasons and came back for the last two. Perhaps the most eclectic were those worn by Emilia Clarke in her role as the doomed star Daenerys Targaryen. Among the standouts were the complex “Ice Battle” fur and the cape/cloak with a chain and dragon pin in Season 7, which were created to achieve the desired warrior look.
Best Dressed Gallerist: Lucy Chadwick
The London born Brooklyn based gallerist is not only a beloved and highly respected figure in the art world; she has become a “reluctant” style star owing to her keen eye and cerebral approach to dressing. The Oxford College and Central Saint Martins graduate has a proclivity for tailored, richly textured clothes, button-down shirts, and vintage Levi’s.
Her love of art inspired, graphic pieces (such as those seen here by fellow St. Martins alum Raf Simons for Calvin Klein 205W39NYC) are in perfect harmony with her ever-changing but always colorful and artistic environment.
Best Dressed Entrance Maker: Lady Gaga
Lady Gaga has had quite the banner year, and she has the grand entrances to prove it. She not only won a Golden Globe for Best Actress in “A Star is Born” but was hands down best dressed that evening in custom blue Valentino.
While she didn’t win an Academy Award for her starring role in the movie, she looked every inch the star that evening, and went home with “Best Original Song.” Of course, she could have won “Best Performance at the Met” with her well-choreographed grand entrance and elaborate 4 wardrobe changes that evening.
Best Dressed with a Baby Bump: The Duchess of Sussex
For most mere mortals, it’s quite a challenge to figure out what to wear and how to look stylish while pregnant. But new mom Meghan Markle, The Duchess of Sussex, did just that. With her dazzling maternity wardrobe, she has proved that you don’t have to sacrifice style when you are expecting.
Regardless of the event or the occasion, she remained true to her panache selecting the chicest, most flattering, most minimal clothes AND the highest of heels (well, she doesn’t have to worry about running to catch a cab after all!).
Among the standouts: the white cotton button-down shirt and high-waisted floor-length black Givenchy skirt with a side slit worn to the 2019 Endeavor Awards and the elegant white Calvin Klein dress and Amanda Wakeley coat selected for a gala performance at the Natural History Museum in London.
Best Dressed and Most Courageous: Selma Blair
It would have been easy for Selma Blair to hide the diagnosis with Multiple Sclerosis (MS) she received in August 2018. Instead, the 46-year-old actress is sharing her journey with the world and looking stunning doing it. She made her first public appearance walking the red carpet at the Vanity Fair Oscar Party wearing a flowing Ralph & Russo color-block chiffon dress and cape and using a custom embroidered cane as a chic accessory.
In April, she was honored at the 26th annual Race to Erase MS Gala, arriving with her adorable son wearing a Christian Siriano tuxedo. The star might need a cane to help walk, but she has proved that regardless of how severe this disease is, she is tougher, and a fighter.
Best Dressed Perfumer: Tom Ford
Tom Ford’s formal correctness is legendary; his idea of ‘Dressed Down Friday’ is a velvet dinner jacket with fabulous turquoise jewelry, and nobody looks as “Fucking Fabulous” in a tuxedo. Speaking of which, the fashion designer, film director, film producer and newly installed Chairman of the CFDA is also an award-winning perfumer.
He has created some of the most iconic scents in the world for which he was honored with the Hall of Fame Award at the 2019 Fragrance Foundation Awards. And yes, he was wearing a tuxedo!
Best Dressed in Court: Cardi B
Last year, Cardi B was charged with assault and reckless endangerment in connection to an altercation at a New York strip club. The 26-year-old record-breaking rapper rejected a plea deal and has proclaimed her innocence. And she has announced, “It’s a crime NOT to look good at all times, especially in court” with her uncharacteristically classic wardrobe, which was obviously planned and well thought in advance of her various court appearances.
The one thing the famed rapper refused to tone down was her manicure. After all, she wouldn’t be Cardi B without those famous acrylic nails which make a statement on their own.
Best Dressed in Leggings: Vanessa Friedman
Leggings were a hot topic and became a “cultural lightning rod” this past March after Maryann White, a mother of four sons, sent a letter to the University of Notre Dame pleading with female students not to wear them because they were too form fitting and suggestive. This prompted Vanessa Friedman to weigh in on the subject, with her article, “It’s Possible Leggings Are the Future. Deal With It”, April 1, 2019.
As it turns out, leggings form the basis for The New York Times fashion director and chief critic’s own chic evening wardrobe. She wore them to several high profile evening soirees in the past year, including the 2018 Fashion Group International Night of Stars for which she was honored with the Media Award.
Best Dressed Style Influencer: Olivia Palermo
The 33-year-old business woman, entrepreneur, and designer has 6 million Instagram followers. She has been called “The Original Influencer” thanks to her impeccable and unparalleled approach to style. She has become a front-row fixture at Fashion Week here and abroad, not to mention the bi-annual haute couture showings in Paris.
She always tries to show her support for the designers whose shows she is attended by wearing pieces from their collection but still manages to stay true to her personal style. Olivia said she chooses what makes her feel like “the best version” of herself at the time and rarely wears one designer from head-to-toe. She is pictured here wearing Schiaparelli leaving the Schiaparelli show in Paris and Valentino at the 2019 ABT Gala.
Best Dressed at Cannes: Elle Fanning
At the age of 21, Elle Fanning was the youngest Cannes Film Festival jury member, but she proved to be wise beyond her years in terms of her savvy fashion sense. She wowed with her choices for the prestigious Cannes Red Carpet, particularly the moment she channeled old Hollywood glamour and recreated the New Look in a Dior ivory silk organza shirt, midnight blue tulle skirt and wide-brimmed hat.
But having great personal style is not just about glamorous red carpet moments. Elle was impeccably turned out from the moment she arrived at the airport wearing a Prada pantsuit, and was effortlessly stylish through the week as she stepped out in several different daytime looks; all of which were appropriate and suited her to a ‘t.’
Best Dressed Documentary: Halston
Roy Halston Frowick died in 1990 at 57, of AIDS. He was the first American superstar designer; the father of minimalism who revolutionized fashion with his deceivingly simplistic bias cut satin dresses that elegantly floated over the body and were made for dancing. Frederic Tcheng’s new documentary, Halston, explores the award-winning designer’s rise to superstardom in the 60’s and ’70s and his ultimate downhill spiral in the ’80s.
It is narrated by Tavi Gevinson and stars Liza Minnelli, Marisa Berenson, Joel Schumacher, Naeem Khan, and Pat Cleveland. But the real stars are Halston’s minimal designs which are revisited through archival clips of past runway shows and high profile events. They are glamorous, elegant, ravishingly sexy, and remain modern to this day. How many designers can take one sheet of fabric and with scissors and one seam, create a beautifully elegant dress?
Best Dressed Doll: Barbie
The number- one fashion doll in the world recently celebrated her 60th birthday and has just been honored with the 2019 CFDA Board of Directors’ Special Tribute Award owing to her wide influence on American fashion and culture and her ability to break boundaries and spark imaginations since her debut. There’s a Barbie to reflect the diverse shapes, sizes, and ethnicities of young people around the world, and this iconic doll has helped to expand the definition of what young women can aspire to.
Through the Mattel Corporation, Barbie has collaborated with influencers like Gigi Hadid and over 75 designers including Tommy Hilfiger, Oscar de la Renta, Vera Wang, Karl Lagerfeld, Anna Sui, Jeremy Scott, and Yves Saint Laurent. She paid homage to the visionary designer modeling three iconic pieces: the 1968 safari jacket, the Mondrian dress created in 1985, and an evening gown from 1983, all in partnership with the Musee Yves Saint Laurent Paris.
Best Dressed and Most Exuberant Benefit: L’hommage: A Night of Celebration, Unity and Love
Fierce, an advocacy group for LGBTQ youth of color, held a cocktail party/vogueing gala in May to raise money and awareness. L’hommage: A Night of Celebration, Unity, and Love, the brainchild of Anthony Stropoli, was held at Judson Memorial Church. Dominique Jackson, Jose Xtravaganza, Javier Madrid and Raquell Lord Balenciaga walked the runway in designs by Ralph Rucci. Pictured above is Jose Xtravaganza and Javier Madrid.
The American couturier also created the gowns worn by hosts Sandra Bernhard and Andre Leon Talley. Ralph said he purposely took a monastic approach to the designs and accessorized with only Elsa Peretti’s chic jewelry and a single cuff from Diana Vreeland, who he believed, would have truly loved this event!
Best Dressed and Picture Perfect: Melania Trump
Fashion is obviously a large part of The First Lady’s diplomacy, and it always sends a message. But politics aside, it’s hard to argue with the fact that Melania Trump is always picture perfect, ready for her close-up, and flawlessly turned out for her public appearances.
I might not always love all her clothing choices, but on her recent trip to London with the President, I did like the white Dolce & Gabbana dress she wore to Buckingham Palace with its prim navy collar, and the matching hat by Herve Pierre, which was tilted just ‘so.’ Not many women could have gotten away with that, but she did. It did not look costumey on her at all, and it did not make me think of Eliza Doolittle in “My Fair Lady”!
It’s no secret that the 49-year-old First Lady loves capes, especially cape dresses for evening. Among the notable examples was this stunning buttercup yellow gown with glowing chiffon cape, by J. Mendel. She looked regal when she wore it to a formal dinner with UK politicians held at Blenheim Palace, in Oxfordshire, England, last summer.
Best Dressed and Gender Fluid: Billy Porter
When it comes to making a grand entrance, and making a grand statement, Billy Porter doesn’t mess around. There is always a message behind his astounding, head turning outfits. At the 2019 Academy Awards, the actor wore a Christian Siriano tuxedo dress and said at the time, “I wanted to create a space where we can have a dialogue about the masculine and the feminine and everything in between”.
At the 73 annual Tony Awards on June 9th, Billy, who won a Tony Award in 2013 for his performance as Best Actor in Kinky Boots, arrived in a head turning red and pink tulle gown-suit combo designed by New York based Celestino Couture. The gender fluid evening suit featured a floral pattern on the train which subtly portrayed female reproductive organs. The actor wanted to make a pro-choice statement about women’s reproductive rights, which are under attack right now. “I am an advocate for all who are disenfranchised” he said.
Photo credits: zimbio.com vogue.com vanityfair.com shutterstock.com fashionista.com time.com eonline.com getty.com nypost.com popsugar.com footwearnews.com dustin pittman people.com flipboard.com hollywoodlife.com