Roger Stone's Eighth Annual Best & Worst Dressed

By Roger Stone

“”It is a very, very foolish thing for a man not to be well dressed” -Lord Chesterton.

It is that time of year when those of us who paid attention to such things recall the tradition of the late Hollywood designer Mr. Blackwell – who, for nearly 50 years, released an eagerly anticipated annual list that began as a chronicle of the world’s best and worst dressed people. The flamboyant, media-savvy Blackwell spared no one — celebrities, movie stars, athletes, socialites and captains of industry were all under his microscope.

Since Blackwell’s death in 2008, we here at the Stone On Style have proudly picked up the torch, continuing this New Year’s tradition, but in its original “Best/Worst” format. It is a proud pursuit, and inasmuch as it truly is a labor of love, it is also an increasingly difficult endeavor, as the state of dress for the public-at-large continues to slide.

We vigilantly monitor the world of media, entertainment, sports, politics, academia, art and fashion to determine who has style… and who truly doesn’t. As an aside, we do recognize that we write this at a time where more gain notoriety for undressing, rather than dressing. The number of naked selfies from actresses and models that have “leaked” drive millions to view the latest celebrity nude.

But alas, we digress. For that is an entirely separate list.

The biggest challenge we face—by far—is filling the ‘best dressed’ category. For people are foolish. There are several rules of dressing that virtually no one follows anymore, and it gets uglier with each passing year. The fact that it really isn’t all that hard to get it right makes it all the more puzzling. First, always be appropriately dressed for the activity you are engaging in. Second, it is vitally important that your clothes be comfortable, and therefore (third) your clothes must fit. Simple, right?

Much of what passes for style today is in fact simply fashion. While style is constant, fashion is temporary. While fashion changes, style remains timeless. There is a difference between style and fashion. Fashion is what you can buy, style is self-expression and how you live. How hard is this, people? Not!

Good taste today was good taste thirty years ago and will be good taste thirty years from now (picture a well cut navy blue blazer with brass buttons). As such, we here at the Stone on Style try to avoid inadvertently lauding the work of any particular stylist or fashion adviser simply for not being dumb.

“Simplicity is the greatest elegance”( Stone’s Rules). It took me some time to figure this out. So we search for those who keep it simple, clean and swank - without being vulgar.

We could go on and on, but it is time to get to the point.

First, some housekeeping.

Larry Kudlow is always on point.

We have bestowed EMERITUS status upon WABC Radio host Larry Kudlow, Sofia Loren, Rolling Stone’s Drummer Charlie Watts, NBC Talking head Josh Mankiewicz, entertainer Andre 3000, Carla Bruni, Jay Z and others who continue to dress with elegance and nowadays just crowd the list. It should never be said that any of the above “did not make the list this year” or anything of the sort, for they are honored and here in spirit until we deem otherwise.

There are many new faces on this years list. And some old favorites have fallen. Justin Timberlake was on the list when Tom Ford was dressing him in a nightclub elegant look that evoked the Rat Pack and 1960′s Vegas. Now, with Ford out of the picture, the exceptionally talented Timberlake has retreated into slovenliness. We happened to catch him live in Miami. He was dressed like the guy who parked our car at the stadium. Terrible. Off the list! So consistency is key. You can change your look but not your taste level! We are always watching…

WTF John Waters?

Jesse Ventura and Michael Moore are beyond hope. We won’t even comment on them further. We have had so many laughs at their expense already it’s just old and sad. This is also not a costume contest, so the likes of Lady Gaga, John Waters, Tim Burton and his peculiar estranged wife Helena Bonham Carter are ineligible for consideration in any form.  Forever.

Bill Clinton made our list- for best dressed- last year after he was seen in a natty spread color shirt. He’s come a long way from being dressed by Donna Karan. Hillary made our list this year- for worst dressed. If she has a fashion adviser he/she should be shot but candidly I suspect she is picking all the wrong clothes herself.

THE BEST

Bob Colacello – Vanity Fair correspondent and the real ‘Most Interesting Man In The World,’ as we like to call him, is the definition of natty. Always tasted, often mono-chromatic and understated. Warholian Republican Colacello also wrote the book on Ronald and Nancy Reagan, with special insights into his close friend and confidante Nancy - who knows a thing or two about style herself.

Audrey Gelman - A bit of an “it” girl at the moment in the Big Apple, this public relations strategist and sometime Democrat campaign consultant has a fresh but sophisticated look that is always sassy but never over the top. Her heavy framed tortoise shell glasses show you she means business. Always correct, but stylish. She wears the clothes, the clothes don’t wear her.

Shannon Sharpe - As a former tight-end for the Denver Broncos, Hall of Famer and Super Bowl Champion, Sharpe may be the best dressed man to ever come out of football. Sharpe, a large and muscular man, shows how good tailoring can convey athleticism without bulk. His shirt and tie choices are bold and solid. Sharpe, who talks sports for CBS on NFL Today, hits the list for a third year. His brother Sterling Sharpe, who we’ve had our eye on, missed the list when he was seen on TV wearing a striped suit - the jacket of which was both too tight and too long. Drop the International Male look, Sterling, and you are IN.

Uzo Aduba - EVERYTHING she wears compliments her body and properly accentuates her busty features. Her red carpet ensemble is simple, understated & elegant. A younger, more attractive and better dressed version of C.C.H. Pounder. We need to catch up on Orange is the New Black.

Prince Philip – H.R.H. hangs on! What a guy. The finest British tailoring. 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 is the gold standard of fine dressing. 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 countrymen, no one can compare with Prince Phillip at Ascot.

Saint John Hunt - Musician, singer, author and son of Watergate Burglar/CIA legend E. Howard Hunt has much in common with last year’s honoree - Reason’s Nick Gillespie. Like Gillespie, Hunt understands the whole “Johnny Cash-man in black” concept. James Dean and Brando got it. Black boots, black pants, black shirt, black jacket. A standard. A uniform. Every day. Every night. Solid. Basic. “Like.”

Idris Elba - It is rumored that he is to be under consideration to play James Bond one day. While we don’t know how we feel about that, it cannot be said that he doesn’t already have the cool 007 style down. He reminds us of a modern day Richard Roundtree. Not flashy. Understated. Perfect. A license to thrill!

Mark Ronson - Rock star progeny, Musician, Producer. A faint Carnaby street vibe. Long term Cary Grant-like potential. Fantastic hair, which always helps.

Mike Smerconish - He used to be more conservative, and frankly, a lousy dresser. But as he has moved from Philly radio to Sirius Radio/CNN his look has steadily improved. He mixes jeans with tasteful sports jackets. His neckwear on camera is solid. Smerconish makes the grade.

Rosie Huntington-Whiteley - A model seen more undressed than dressed. However, when she is dressed, she is smashing! She has the style of Kate Middleton, and an air of sophistication that shows solid long term promise.

Michael Grimm - The soon to resign congressman was always well turned out. Who can forget how well dressed he was when seen on NY-1 cable news threatening to throw a reporter over a balcony. The ex-Marine came on strong to win the Staten Island New York seat in Congress and to win a tough re-election. Then he pled guilty to tax evasion and as of this writing is fixing to resign his seat. Pity that an orange jumpsuit might replace his well cut suits soon enough.

Lykke Li - Swedish songstress Lykke Li often embraces minimalism - allowing her sometimes vintage style to shift from airy bohemian to a darker side that pulls inspiration from Gothic fashion. When it comes to accessories, Li’s eclectic taste helps add personality to her wardrobe. First year on the list, can’t wait to see her in the upcoming Terrence Malick flick.

Eva Green - We could stare at our favorite modern-day Bond Girl and star of ‘Penny Dreadful’ all day long. And sometimes we do. Stylistic perfection is just second nature to this woman.

Daymond John - He dresses for success. This entrepreneur, investor, television personality, author and motivational speaker is so money it’s ridiculous. Pinstripes. Silver ties. Formal. Impeccably groomed. He looks….prosperous. Mr. John does push the envelope at times, however, with the bling. Less metal, please.

Posthumous lifetime achievement award:

Ben Bradlee - The long time Washington Post Editor and sometimes CIA cut-out was a dashing Georgetown cocktail party regular. He said there was no “Deep Throat.” He covered for his pal JFK and exposed the crimes of Richard Nixon. He shed wife #1 Tony, for Sally Quinn. His love of bold English stripes shirts made the film “All The President’s Men.” RIP.

WORST

Hillary Rodham Clinton - The former Secretary of State and 2016 hopeful has no taste in clothing and no idea whatsoever what she looks good in. Take the coat she wore to the Nixon Cox-Castimitidis wedding. She’s changed “looks” more than we have. Darker colors would minimize her bulk, heavy legs and bizarrely thick ankles. Now, this may seem overly nasty and we would agree, except she deserves it. Meow.

Kanye West - GOOD GOD. Yeezus DOES NOT HAVE IT. His wife however, did make our best undressed list when her selfie leaked. Baby got back!

David Boies - The super-lawyer, was recently seen holding a press conference for his client SONY. Did he sleep in that J.C. Penny wash-and-wear suit? Given the huge legal fees he is cribbing from AIG’s Hank Greenberg in a lawsuit in which Boies seems more interested in currying favor with the prosecutors than winning for his client, you would think the man could afford a decent set of threads.

Rand Paul - His ideas interest us. We like his stand on drug law reform, restoration of our civil liberties, and an end to “endless war.” Paul’s clothes? Not so much. The Senator dresses like a college student. He owns no natural fiber garments. His shirt collars never fit. He has been seen wearing sneakers with a suit. The fusing in his pasted together suits has begun to bubble from dry cleaning. Nothing is pressed. NOTHING. And that hair gel. Ghastly. To have a shot at being President, he has to begin dressing like one.

Madonna - She’s has lost it. This from a fan of the Material Girl. Blonde Ambition Tour. Evita. We have loved every incarnation, BUT this one. A dental “grille”? Really? She’s like a ghoul.

Guy Fieri - Has this guy changed his clothes since 1994? Dresses like an overweight beachcomber who lives near a Hot Topic. The Fu Manchu ‘stache is bad enough. We imagine him to be ketchup stained. Probably has Crabs.

Bruce Jenner - How bad can it get for this obviously cuckolded Olympic gold medal winner? He is on our worst dressed women’s list. Did you see him in women’s clothing on the cover of the National Enquirer? Hi, bag lady!

Bono – Seriously. Go away.

Taylor Swift – Shush. The woman has an empire of almost a billion dollars and she dresses like she got everything at a TJ Maxx 30% off sale. This woman is a style train wreck.