2008: Roger Stone's Best and Worst Dressed List

Pulled from the archives: my first best and worst dressed list ever.

Every year, Hollywood designer and arbiter of fashion, Mr. Richard Blackwell, would publish a list of the ten best and worst dressed people in the demimonde. Mr. Blackwell has since gone to his maker, but the STONEzone refuses to let this fine tradition die. Therefore, the Zone has compiled its official list of the best and worst dressed men and women of 2008. However, first a word regarding the sorry state of fashion in America, and the very few who can plausibly claim to be true possessors of style.

If you want to find the best dressed men in America, you must go into the nation's statehouses where the lobbyists and titans of special interests sport impeccable suits with classic, refined, and conservative styling. The starchy lawyers aside, lobbyists are the only elegant men left in America. They veritably live night and day in their suits, which is fundamental to the art of looking good in one.

If you want to find the worst dressed men in America, any corner bar should suffice. There you will find men unabashedly wearing baseball hats and tank tops, ill-fitting pants, and blindingly white sneakers. The average American male is an utter disgrace to male sartorial tradition. The ubiquitous gangsta fashion craze alone is enough to nauseate any person of even minimal taste, but the Ashton Kutcher trucker hat craze truly moved American men to the bottom of the fashion rung. To wear a hat indoors, especially a baseball hat, is a veritable fashion felony. It advertises not only bad manners but also poor taste. Ladies, my condolences.

While a true expression of the gold standard in mens personal style, sprezzatura informs the success of the best-dressed woman as well, if to a lesser degree. That's because men dress, but women dress up. And we like it that way. So for the ladies, wearing an air of effortlessness is just as important as for the men. But a little affectation--even daring--is not only forgivable in woman's dress, it is often roundly encouraged. Everything else matters in just the same way it does for men--fabric, cut, MORE, MORE. The woman who understands how to wear great clothes naturally is always the best-dressed person in the room.

A list of best-dressed women written by a man is bound to bear the watermarks of an age-old truth about the male worldview: A woman's clothing is a kind of mental foreplay for men. Being dressed is what comes before being undressed, which is always a pleasure to think about. Just by way of explaining some of the notables on the list below.

The problem of course is that most men just don't care and don't care to learn.

SPREZZATURA

In 1528, Baldassare Castiglione in The Book of the Courtier coined the term "sprezzatura". He wrote:

Avoid affectation in every way possible . . . practice in all things a certain Sprezzatura, so as to conceal all art and make whatever is done or said appear to be without effort and almost without any thought about it.

Therefore, the key is not a closet full of expensive clothing, but rather to look like you haven't thought about what to wear, even though you look great. A look must never be studied or too precise; it should be nonchalant, even insouciant. Gary Cooper had it. So did Sir Anthony Eden, Douglas Fairbanks, Jr., John Davis Lodge, Cary Grant, and Ambassador Henry Catto.

Sifting through those in sports, academia, politics, government, entertainment, and media, it's hard to find people who are truly well-dressed as opposed to those whom a wardrobe producer merely outfits. Fred Astaire didn't just look good in his movies- he looked good all the time. Contrast Astaire with Jeremy Piven of Entourage. I suspect his "Ari Gold" look is not his taste but that of a costumer. Piven at leisure seems slovenly.

The rules are simple, yet few men follow them. The elements of dress must exude confidence in one's choices. Poor grooming must not detract from your appearance; gentlemen shave those pornstaches. Match your suit to both your body type and age. Find a top-notch tailor and use him (or her). Learn about fabric and choose only those of top quality and appropriate weight for your climate. Trousers should hang from the waist and have a proper break. A suit without cuffs is appropriate, only if you are a gigolo or in a show band. No over sized jewelry of any kind, particularly cuff-links. Match patterns carefully. Black suits are only for chauffeurs and funeral directors. Buy only shoes of the highest quality leather or suede and leave the sneakers in the gym. Lastly, learn to like looking good.

That said, here they are: