The notion of ‘Best Dressed’ is elusive and highly subjective. It means different things to different people. It means different things to me at different times, and depending on the context it’s put in. Best Dressed, like beauty, is indeed, in the ‘Eyes of the Beholder’! I’ve sometimes been tempted to make a most beautiful list, but beauty, which is both inside and out, is not just about possessing certain God-given assets (which certainly doesn’t hurt). It’s about the entire package: your soul, your essence, your humanity, your grooming, and how you present yourself to the world (in other words, what you wear). You can’t separate these elements. So you could say that my Best Dressed List is also my “Most Beautiful List.” I could not agree more with Iris Apfel, who said it’s far more essential to possess great personal style than physical beauty. After all, beauty fades, but style is forever.
I try to steer clear of those who made my past lists because they would invariably be on my lists 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. I try to vary my categories from year-to-year. See our past 2017 “New” Best Dressed List; 2016 “New” Best Dressed List; 2015 “New” Best Dressed List; 2014 “New” Best Dress List; and our first 2013 “New” Best Dressed List.
This time around I wanted to focus on diversity concerning ages, backgrounds, lifestyles, occupations, races, genders, body types, and fashion styles and hone in on specific niche categories as they applied. If there is a thread that holds this group together, it is that they each have an identifiable ‘look’ and a specific point of view, as captured in images culled from the past year.
In completely random order (click images for full-size views). Photo credits: Getty.com Zimbio.com Vogue.com Vanity Fair.com Just Jared.com eonline.com people.com redcarpet.fashionawards.com yahoo.com:
Best Dressed Democratic Socialist: Alexandria Ocasio-Cortez
Less than one year ago Bronx native Alexandria Ocasio-Cortez was waitressing. The 28-year-old third generation New Yorker has quickly gone from working-class activist to a congressional candidate and history-making winner of the most significant U.S. election upset of the year, defeating Democratic Rep. Joe Crowley for his seat in Congress. The woman considered to be The Next Big Thing in the Democratic Party believes firmly that “in a modern, moral, and wealthy society, no person in America should be too poor to live.” While fashion is hardly her primary focus, she is always appropriately turned out, looking polished, highly professional, and ready for action. She relies on a minimal, clean-lined unfussy wardrobe comprised of versatile and urbane pieces in black, navy, and ivory with an occasional hit of color. She keeps her accessories to a minimum, her hair sleek (it’s often pulled back in a low bun), and has been known to add a red lip and manicured red nails as a punctuation mark.
Best Dressed in Coats: Anna Wintour
If “fashion is the armor to get you through the paces of your everyday life,” according to the late Bill Cunningham, coats are the ultimate fashion armor. For the 69-year-old Vogue Editor-in-Chief and Conde Nast Artistic Director Dame Anna Wintour, they are as much a part of her intimidating armor as her Chanel sunglasses and her every hair in place bob and as much of a signature as her ever-present antique Georgian Collet necklaces. Ms. Wintour understands the importance of having a wardrobe of coats. She wears them well and with authority, for day or evening. Perhaps her most striking, statement-making iterations are those that match the dress beneath, creating a perfect ensemble, whether accessorized with tall heeled boots or nude Manolo Blahnik sandals.
Best Dressed LGBTQ Icon: Desmond Napoles
Desmond Napoles, whose drag name is Desmond is Amazing, is a performer, drag kid, awarded LGBTQ advocate, outspoken gay youth, editorial model, public speaker, founder of his own drag house, fashion designer, muse, an icon. Most importantly, he is amazing, and he wants kids all over to know that they are amazing too. Desmond began dressing up as a toddler and started wearing dresses by the age of six. He is now 10. One of his defining talents is his ability to work a runway and made his runway debut last February when walking the runway for the Gypsy Sport fall 2018 ready-to-wear show wearing heeled black patent boots, an oversized blazer with a ruffled Renaissance collar accessorized with black and white polka dot nails. He is launching Haus of Amazing, a drag club for ‘drag kids’ and hopes to have a fashion and cosmetics line in the future. His philosophy is “always be yourself no matter what anyone says and even if you get bullied, pay it no mind.”
Best Dressed in Thom Browne: The Cleveland Cavaliers
The Cleveland Cavaliers’ former teammate Dwayne Wade and designer Thom Browne were sitting at Cipriani’s last October before the Fashion Group International’s Night of Stars when Browne had an idea to create custom, matching suits for the Cavaliers to wear during the NBA playoffs in the spring. Star player LeBron James, who was also a loyal client, loved the idea of the team presenting a unified front and he thoughtfully purchased the fabulous threads (the cost was approximately $5,000 per suit) for his fellow teammates. (As if at their hefty salaries, they couldn’t afford them themselves lol).
Who could forget when 33-year-old James showed up wearing Thom’s cropped shorts, striped socks, and an alligator bag that cost $41,000 right before the NBA championship finals on Sunday, June 6th? His picture was literally all over the internet, in the newspapers, and even made the evening news. Of course, last month, James announced that he left the Cavs (he signed a 4-year $153.3 million contract with the Los Angeles Lakers). I wonder which team will now have ‘custody’ of Thom Browne’s gray suits! Meanwhile, it seems Thom is now onto another sport. He is reportedly partnering with Spanish football club FC Barcelona in hopes an assist from the sporting world will help fuel brand growth.
Best Dressed in Evening Tailleur: Janelle Monae
It is a well-documented fact that women who show up at soirees wearing impeccably tailored jackets and pants can easily outshine those wearing a more predictable and traditional evening dress. One woman who knows this better than anyone is the 33-year-old singer, songwriter, actor Janelle Monae, whose uniform for high profile events almost always consists of some version of a tailored jacket and pant. Her “dedication to uniformity” (as she calls it) is also apparent in her chosen color palette. While she has begun to add a pop of color (red), she almost always relies on black and white, which for her, is a way to honor both her parents, who were working-class people.
Best Dressed in Ball Gowns: Jean Shafiroff
Nobody is as associated with ball gowns, or wears them with as much verve, enthusiasm and commitment as philanthropist, businesswoman, and author Jean Shafiroff (her first book, “Successful Philanthropy: How to Make a Life By What You Give,” is an inspirational and comprehensive guide to giving). She wears a variety of labels, but among those, you will likely see her in quite often are Oscar de la Renta, Carolina Herrera, Dolce & Gabbana, and customized designs by B. Michael and Victor dE Souza, for whom she is a muse. She is not afraid to repeat, has fun with fashion and sees fashion as an art form. Her full-on ball gowns are quite grand and entrance making, and while they are as notable as her tireless charity work, she is always quick to emphasize that it is her philanthropy and humanitarian efforts, which are her top priority.
Best Dressed Supreme Court Justice: Ruth Bader Ginsburg
The 85-year-old champion of women’s rights is the second female justice of the U.S. Supreme Court (after Sandra Day O’ Connor) where she has sat for nearly 25 years, and one of four to be confirmed. Her feminist legal work in the 70’s was immortalized in the movie, RBG (she was portrayed by Natalie Portman). The Supreme Court justice has spent a lifetime breaking female stereotypes and fighting for equality, and she has a very strong sense of self. She keeps her 5’1” frame in shape through intense workouts with a personal trainer and does not shy away from fashion, either on or off the bench. Her hair is always neatly pulled back in a low ponytail, held in place by one of her many fancy scrunchies and she has apparently started a trend (Mansur Gavriel showed the much-maligned hair accessory the runway for spring 2018 and Balenciaga was selling one for $195). She has even found an inventive way to personalize her black robes: by adding an assortment of elaborate lace collars and an array of different gloves.
Best Dressed Teenager: Millie Bobby Brown
But then again, Millie is not just another teenager. The 14-year-old is not only a gifted actress, having initially burst on the scene in the Netflix series Stranger Things, but she has also attracted the attention of the fashion world owing to her excellent fashion sense, which has been apparent in her many public appearances and red carpet outings. Millie was only 12 when she signed with IMG models, and she has starred in Converse and Calvin Klein ad campaigns (she is a muse for Raf Simons). She continually proves her range and can pretty much rock anything, looking as natural wearing a sporty ensemble by Nicolas Guesquiere for Louis Vuitton (cool sneakers included), or dreamy couture like a strapless dress with full tulle skirt by Calvin Klein By Appointment. Her choices (down to the accessories) are not only exciting and varied, but informed, and most importantly, they are always age appropriate; everything has to pass muster with both her mom and dad (she said that if he doesn’t like it she won’t wear it!) It will be fun to watch as she gets older and more experienced.
Best Dressed Head of State: Theresa May
The 61-year-old Prime Minister of Britain and leader of the Conservative Party since 2016 is only the second woman to hold the post in Parliament. She may be politically conservative, but not when it comes to fashion and style. Her bold wardrobe choices exude pride and confidence and at 5’8” she has the stature to wear clothes well. She is especially known for her love of accessories, from statement-making beads and belts to her ‘fun’ shoes: colorful and leopard print flats and kitten heels. They not only add personality and interest to her otherwise classic and tailored ensembles, they admittedly make her happy. At the Women in the World Summit last year, she admitted, “I like clothes, and I like shoes. One of the challenges for women in the workplace is to be ourselves, and I say you can be clever and like clothes. You can have a career and like clothes”.
Best Dressed at a Movie Premier: Sarah Paulson
The award-winning 43-year-old American film, television, and stage actress is a known risk taker as exemplified by the bold roles she selects and that also holds true for her fashion statements on the red carpet. While she has always exhibited great style, this past year, she has really slain it. As one of the stars of the all-female cast of the movie ‘Oceans 8’, she has attended her share of high profile premiers as of late, and her choices have been unusual, exceptional, edgy and unique to say the least. Two moments that really stood out were the ‘Oceans 8’ New York premiere, where she literally dazzled in a fluorescent green sequined and fringed Prada dress from fall 2018 (she referred to the color as “highlighter”) worn with small gold hoop earrings and a green wrist-let. For the London premiere, she went in another direction entirely and opted for a pink scalloped and asymmetrical dress from the Valentino fall 2018 ready-to-wear collection. With a red lip and her hair slicked back, she accessorized with only dangling pink floral earrings.
Best Dressed in the Same Dress: Tiffany Haddish
Even though Tiffany Haddish is riding high these days, and can well afford to splurge on whatever she wants, she is intent on getting a big bang out of her buck. The comedic host has made no secret that she is obsessed with getting a lot of mileage out of her $4,122 white Alexander McQueen halter dress. As she put it, “I feel like I should be able to wear what I want, when I want, no matter how many times I want, as long as I Febreezed it,” Haddish said of her dress. She spent a lot of money on that dress, and she won’t wear it just once. In fact, she has worn it in public four times. She originally wore it at the “Girls Trip” premiere last summer, while hosting “Saturday Night Live” in November, at the 2018 Oscars, and most recently while hosting the MTV Movie & TV Awards on Monday, June 18th. I love that each time, she styled it a bit differently, changing her hair and accessories and while I applaud her commitment, I think it’s time to retire the dress and start wearing some other designs in the future.
Best Dressed in a Button Down Shirt: Victoria Beckham
Those who possess personal style don’t just look great for special occasions, but all the time. Designer Victoria Beckham certainly has many high profile soirees, but it is her laid-back off-duty style that gets my vote and really appeals to me. The busy 44-year-old mother of three and wife of David Beckham always exudes confidence and natural ease in her ‘uniform’ of slightly over-sized borrowed from the boy’s button downs most often paired with slouchy high waisted pleated trousers or maxi trouser skirts. They are sometimes worn beneath a perfectly tailored jacket or worn on their own. I love their offhanded tomboyishness and the way they perfectly offset her uber-feminine visage, providing a beautiful contrast to her delicate fine-boned frame (she stand 5’4”). Regardless of which bag she carries or her choice of footwear (from ultra-elegant high heeled pumps to sturdy flat sandals and classic white sneakers), she invariably accessorizes with oversized shades and a gold bracelet watch, and always looks chic and pulled together.
Best Dressed Red Carpet Chameleon: Zendaya Coleman
Singer, dancer, actor Zendaya is just like a box of chocolates, you never know what you are going to get. When you see her, it is always a surprise; she can look completely different, from the fashion to the hair, to the point of being completely unrecognizable. At 5’ 10”Zendaya can virtually wear everything, and at the ripe young age of 21, can get literally get away with anything and pull it off! She clearly loves fashion, is fashion savvy, and has great fun experimenting and she is fun to watch. Two recent examples of how she can go from one extreme to the other: she channeled Joan of Arc in a fierce armored Versace gown for the Met Gala. And just a few days prior, she looked elegantly beautiful paying homage to the iconic Tiffany & Co. shade wearing a billowing mini dress and black satin headband at the Tiffany Paper Flowers jewelry collection launch party at their Fifth Avenue flagship store.
Best Dressed in Ralph Lauren: First Lady Melania Trump
The First Lady can afford everything, and as a former model, at a statuesque 5’11” she can wear it all. She understands the power of fashion and how it can send a message (except for that Zara jacket of course), and she understands the importance of dressing correctly and appropriately for every occasion. Melania wears a variety of labels (the best the fashion world has to offer) and intuitively knows when to wear American. While she almost always knocks it out of the ballpark regardless of the occasion, I happen to really love her in luxurious American sportswear and what designer epitomizes that more than Ralph Lauren? I can’t think of another woman who wears the iconic label so well and so authoritatively.
Best Dressed Newlywed and Newly Royal: Meghan Markle, the Duchess of Sussex
It can’t be easy to be newly married and living in a foreign country, and notwithstanding the apparent perks and advantages, it most certainly can’t be easy to instantly transform oneself from a commoner to a full-fledged royal. But Meghan Markle’s new life seems to really suit the former ‘Suits’ star. The world has been watching her every move, and scrutinizing and critiquing all her fashion choices ever since her engagement to Prince Harry was announced last year. While she shined on her wedding day and was undoubtedly a gorgeous bride in her minimalist Givenchy gown, she has had a few hiccups along the way, with clothes that were ill-fitting and too busy for her small frame. She looked as though she was trying too hard.
But Meghan has got it together and is really hitting her stride with a sophisticated look that focuses on cut, fit, and structure. She is regal yet relaxed, befitting her American heritage. She is the epitome of modern, elegant simplicity whether clad in sportswear separates, tailored pantsuits, sculptural sheaths, or perfect little black dresses from labels such as Givenchy, Dior, Ralph Lauren, Roland Mouret, Stella McCartney, Emilia Wickstead. She even manages to look fabulous in a hat (a requirement for a royal), and that is no small feat!
– Marilyn Kirschner
