Stone’s Style’s 2011 Best and Worst Dressed

Posted on December 31, 2011 by Roger Stone

For nearly 50 years, Mr. Blackwell of Hollywood sat as an arbiter of fashion by publishing a yearly list of the 10 Best and Worst Dressed People in the Demi-monde. Although best known for his “Worst Dressed”list, he maintained a successful career as a fashion journalist. Richard Blackwell was a powerful syndicated columnist who wrote features in newspapers and lifestyle magazines. Matrons and starlets, stockbrokers and models, politicians and prize-fighters all jockeyed to be included. Blackwell’s critiques could be cutting. Being included in Mr. Blackwell’s Best Dressed list could quickly improve one’s social standing in New York, Miami or Hollywood while being included in his worst dressed list could doom one to social Siberia.

Although Mr. Blackwell has gone on to his maker, we here at the STONEzone revived this hallowed tradition four years ago. We have vigilantly watched the world of entertainment, sports, politics, academia, art and fashion to determine who has style….and who truly doesn’t.

Therefore, we proudly present our FIFTH ANNUAL 10 BEST AND WORST DRESSED PEOPLE IN AMERICA list for your consideration.

Compiling such a list is a far greater challenge than one might think. The advent of “casual fridays” is symptomatic of an overall decline in our standards regtarding what is right and wrong about the way Americans dress. Sadly, fashion today is more motivated by economics than aesthetics. Men are seen in both business and social settings in running shoes, tracksuits, sweats, T-shirts, and caps, which advertise either a sports teams or a brand of farm tractor. Women are seen outside the gym in spandex workout ensembles and hoodies. Women actually leave their homes with a Victoria Secret slogans on their ass.

Americans cared deeply about proper dressing in the 1930s, 40s and even the 50s. The 60′s, a decade fashion forgot, also began a trend of informality that devolved over time from slovenliness in the 90′s to dishevelment in the 2000′s. The sheer number of men who will go out in public in a wife-beater is staggering. Very few can look like a young Marlon Brando but men still crowd casinos, bars, malls and sports events in this “outfit.”

Our goal is to sort out those who are merely fashionable from those who possess real style, for fashion is fleeting and style endures. We also try to eschew “costume.” That’s why you won’t find Lady Gaga or Tom Wolfe on our list. While both are distinctive in their dress, both are affecting a costume more appropriate for the stage. While fashion is about fads and what is “in” now, style is a personal factor that cannot be learned or taught – either you have it or you don’t.

Style is, in fact, the direct opposite of fashion. Fashion is a look that is temporarily “in”. Fashion is people imitating each other. It’s about fitting in and looking like everyone else’s Style. Fashion, on the other hand, is about individuality; what sets one apart from the crowd. Real style comes from within; it is the sign of your character and personality that you display to those who see you. Style never indulges fads or gimmicks.

Style is timeless. Style looked good thirty years ago and will be in good taste thirty years from now.

True style is never studied. It manages to make it’s own statement heard above the temporary fads of fashion. Style requires good taste, individuality and a certain nonchalance, what the Italians call “Spezzatura.” It is the art of dressing distinctively without looking like any thought or planning has been put into the final look. Being “thrown together,” but perfect. It is said hoofer Fred Astaire threw his new custom made fine cut English suits against the wall repeatedly to “knock the newness out of them”.

Finding our 10 Best and Worst Dressers requires careful study. The dressing of our citizens hasn’t improved much in 2011. There are among us no Jack Kennedys or Gary Coopers, no Katharine Hepburns or Marlene Dietrichs, Instead we have Cee Lo Green, Jack Black, Snooki, or anyone of the Kardasians.


Joseph Gordon Levitt – The hot young actor is new to the Best Dressed list. He’s developing a personal style that evokes a cool updated 50′s Rat Pack look. White short point collared shirts, skinny black ties, narrow lapels with dark fitted suits teamed with a pork-pie hat mark Gordon Levitt as a hipster but a perfectly turned out hipster at that. He pulls of the monochromed shirt-tie-suit look without looking like Joe Pesce in the movie “Las Vegas”.

Charlie Watts – When band-member Mick Jagger was wearing sequin tights and oversized Uncle Sam hats, the Rolling Stone’s drummer was quietly going to Poole and Dege, two of Savile Row’s oldest tailors. The result is somber, perfectly-fitting and low key suits that are as solid as his back-beat. Watts is as fastidious as Keith Richards is disheveled.

Larry Kudlow – The CNBC Talk Show host and ardent supply-sider makes our list for the fourth year in a row. Kudlow’s sense of dress shirt, suit and tie combination is always right, and interesting. Kudlow show some whimsy with pink and patterned neckwear. New York Tailor Leonard Logsdail makes Kudlow’s impeccable fit. The knot of his necktie is always so. The economic analyst and pro-growth advocate sets a standard other men can aspire to.

Gordon Woodrow – The long time top level Republican U.S. Senate staffer, Presidential appointee and businessman dresses like a country squire. He teams hefty tweeds with tattersall, checks and plaids and brown suede shoes, sometimes with a bright sweater-vest. Large knots the size of your fist in heavy wool ties. Woodrow always looks like he just came from shooting grouse or skeet on the Moor.

Prince Philip – Husband of the Queen Elizabeth II. Prince Phillip, born Prince Philip of Greece and Denmark, The Duke of Edinburgh, is long-time a client of Gieves & Hawkes Ltd, the venerable London tailor who’s house style has military lineage. Phillip, father of Prince Charles, who prefers a double-breasted look made for him by Anderson and Sheppard, was rushed to the hospital with chest pains only weeks ago. The Duke has his dashing military dress uniforms made by Johns & Pegg Ltd, his kilts by Kinloch Anderson Ltd, and shoes and boots by John Lobb. Affectionately called “Charlie the Greek” by his country-men, no one can compare with Prince Phillip at Ascot. We wish him a speedy recovery from heart surgery.

Alan Flusser – The men’s wear designer Alan Flusser knows more about men’s clothing than perhaps anyone in the world and his taste level and flair make him the authority. Author and arbiter Flusser is an advocate for all that is correct and refined. Flusser is the designer other designers secretly emulate. The late saloon singer Bobby Short, a debonair dresser himself, consulted Flusser. Whether in a double breasted beaded stripe suit or with a scarf knotted ascot-style around his neck, Flusser is sartorial perfection.

Johnny Depp – Second year on the list. Last year we said “Now, rockers and actors, and those in the creative field can get away with things the rest of us cant, but Depp’s dark look, his affection for hats and a minimal but tasteful jewelry land him on the list. Scruffy but never too scruffy, it’s a look Depp has perfected. “No one has looked this good in a short brimmed straw fedora since Sinatra.

Jacob Stein – Few men can pull-off the bow-tie without looking like Pee Wee Herman or Malcolm X. Fox Talking head Bob Beckel from “The Five” was recently on-air with what appeared to be too perfect clip-on. Only clip ons that squirt or spin should been worn and then only if you are a comedian. Bow ties should never be perfect or prissy. They should be slightly askew, tousled and imperfect. Washington power lawyer Jacob Stein, lawyer for Monica Lewinsky, pulls this off like nobody else. Seen on K street, the dapper Stein always looks great. The DC barrister’s wife owns a consignment shop and Stein clearly choses quality vintage pieces to mix into his traditional wardrobe.

Dave Beckham – Great tailoring is meant to hide imperfections, making the fat look thinner, the short look taller, hiding a paunch etc. In Dave Beckham’s case none of that is necessary. His body and level of fitness are incredible. Not every man can wear a vest (what the Brits call a waistcoat) without looking like a riverboat gambler or John Foster Dulles. Beckham pulls them off along with smartly cut suits, newsboy caps, classic aviator sunglasses and perfectly tied scarfs which make him stand-out when he’s he not semi-nude or in a soccer uniform.

Josh Mankiewicz – Hitting our list for the second year, this NBC Dateline reporter tops Brokaw, Lauer and Williams. His two-button natural shoulder suits are always fastidious, his shirts and ties chosen with care. His look is quiet, understated and always low-key. The length of his collar points chosen to compliment his face, are always accented with the perfect pocket-square in a puff that looks like he stuffed it in his breast pocket without a thought.

Bill Clinton – The ex-President wasn’t much of a dresser when in the White House, buying off-the-rack and wearing the clothes of Donna Karan, who designed what a woman thought a man’s clothes should look like. Since his heart surgery and becoming a vegan Clinton’s inner pea-cock has revealed itself. Clinton has largely dumped the big shouldered double breasted suits than made him look blocky for three piece-models that accentuate his weight loss. His new look is dignified yet natty–what we want an ex-president to look like. Check out Clinton’s photo on the cover of his new book which outlines a path ahead for America and is designed to submarine Obama, who Clinton neither likes or respects – deep blue suit, silver tie and perfect fitting vest. Hail to the Ex-Chief!

LIFETIME AWARD: Willie Brown – From his hand-crafted Brioni suits to his extensive collection of hats, the former California Assembly Speaker could be the best dressed man in America. While most men should avoid brown as a suiting color (Philadelphia Brahmin Biddle was once asked why he had over 200 identical bespoke blue suits. “Because brown looks like shit,” he replied) Willie brown pulls it off in both double-breasted and three piece vested models. As Mayor Brown sometimes changed clothes as many as four times a day for his various public ceremonies. A master of color-coordination, Brown’s shoes, suit, shirt, necktie, hose and chapeau always complement each other.

The Worst Dressed Men of 2011

Michael Moore – Looks like he slept in the Occupy Wall Street tents even though he didn’t. Looks like he slept in his clothes and might have. The man gives the word “slob” new meaning. Oversized sweatshirts just make a fat guy look fatter. Slovenly. While we’re at it, how about a shave?

Larry King – Thank God, this man is done in primetime. What is with the black shirt, black ties, black suspenders look? Who does Larry think he is – Johnny Cash? Even worse – the black shirt and white tie. Even Lucky Luciano wouldn’t wear that. Larry actually wears clip-on suspenders. Clip-ons. Wise up Larry.

Simon Cowell – Fourth year on the WORST list. Man-boobs should be hidden not accentuated . This guy still looks like a wax pear that sat on a radiator too long. I swear he is buying out of the International Male catalog. A pinstriped suit with a shawl lapel? He’s from the U.K and can afford the best. Rush this man to a proper tailor.

Jesse Ventura – Since leaving the governor’s chair he looks like a homeless Hulk Hogan. The bald with a ponytail look is so…still bald. Jesse wants to be the Libertarian Party nominees for Vice President but there is no real support for him. Hint: If you are going to go on TV with outlandish conspiracy theories don’t wear outlandish clothes and try washing your hair occasionally.

Chuck Schumer -This guy is a schlub. Schumer has been seen in the Senate wearing the same baggy-kneed, wrinkled suit and dress shirt and pilling sweater vest three days in a row. New York has some of the greatest tailors in the world. The senior senator needs to call one. Daniel Patrick Moynihan, who once held a US Senate seat from New York, was a dandy who fancied bold striped suits, polka-dotted bow ties and jaunty Irish walking hats. Schumer dresses out of the Salvation Army.


Natalie Portman could wear a garbage bag with an old rope around the waist for a belt and still look stylish. Portman is just one of a growing number of celebrities whose basic budget-friendly choices make them seem more relatable and down-to-earth than stars who drop thousands for a single, wear-it-once dress so fashion consultant picked out. For last year’s Golden Globes she chose a simple pale pink dress decorated with a large red rose which flattered her body shape perfectly, a red Dior clutch and a pair of red platforms. Always well put together and elegant.

Pippa Middleton – Philippa Charlotte “Pippa” Middleton, the English socialite and younger sister of Catherine “Kate” Middleton embodies the best in English style and has elbowed her sister off our list this year. Since she was the maid of honor at her sister’s wedding to Prince William she’s surpassed her sister as a style-setter in the U.K. Some say she has a perfect derriere and in jeans, a mini-skirt or a party dress it seems so. Take that Kim Kardashian!

Blake Lively – The Gossip Girl star has legs that go on forever. If she’s sporting a short skirt she hides the cleavage. If showing the decolletage she sheaths her legs in a long dress – in other words, Lively knows when too much is too much. Liveley knows purple just “works” for her as a color and she wears it a lot-meaning she knows what she looks good in.

Carly Foulkes – You know her as The T-Mobile Girl. The Canadian-born model and actress wears a summer dress like no one else. Foulkes is the “picture-perfect” brunette. Saucy, stylish and comfortable, she could get us to buy a phone or just about anything else. Always looks like she’s ready for a picnic on a beautiful day.

Carla Bruni – The wife of the French President has a style that is continental, chic, and understated. Although Italian she may be the single best ambassador for French couture. Her look is spare and simple and accentuates clean lines. No flashy or bright colors works for her. Blues, grey, charcoal. Cutting edge chic.

Sophia Loren – Although she is seldom seen in public these days, when she is seen she wears high end Italian couture like no one else. This raven haired beauty is somehow sexier in her clothes than she would be au natural. If you have seen photos of her in a garter belt and silk seamed stockings, you have seen feminine perfection.

Eva Mendez – Two Latin spitfires make our list this year. For Sofia Vergara look below. Let’s face it. Mendes could wear a shower curtain and she would still look good. The woman oozes sex yet never makes it tawdry. Ms. Mendes has a skin tone that allows her to choose any color, but which works particularly well with pastel colors. Mendes knows her body and selects outfits to accentuate it. Mendes is sultry and stunning, always.

Emma Watson – A stylish little hottie, the English actress who broke through in the Harry Potter films has graced the covers of Teen Vogue, the UK’s Tatler and Italian Vogue. Watson cares about clothes and supports the British Fashion Industry in high style. Her choices are sure-footed. She has twice been chosen as the face of Burberry. Twiggy and Mia Farrow never looked this good in closely cropped hair.

Jennifer Aniston – This woman knows what she looks good in. She sticks to a short skirt and strappy heals because she knows it looks best on her. She rarely changes her hairstyle because she has a looks that works for her and sticks to it. Aniston has always been an example of impeccable style and hardly ever gets it wrong with her looks, both on and off screen.

Sofia Vergara – Usually seen on the arm of boyfriend, banking heir and someday politician Nick Loeb, Vergara has a strongly Latin influenced style that always has her looking chic on the red carpet or on the streets of Manhattan. The star doesn’t shy away from her signature curve-hugging clothing. Equally stunning in jeans, dresses and colorful tops, Vergara wouldn’t be caught dead in cut-off jean shorts proving you can be sexy without being vulgar.

The Worst Dressed Women of 2011

Snooki – Last year when we said his girl has “a big all natural Italian rack” we were inundated with complaints. Seems the Jersey Shore gal isn’t Italian.

Julianne Moore – Sadly this actress has no sense of coordination and can’t piece together an outfit to save her life.

Christina Aguilera. – When one gains weight one must adjust the size and color of one’s clothes to accommodate. This singer doesn’t seem to understand that. Tight fitting clothing accentuates fat, doesn’t minimize it. A female sausage about to pop.



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