2014: Roger Stone's Best and Worst Dressed List

The 2014 edition of my best and worst dressed list

“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 Years 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 doesnt. 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( Stones 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 Stones 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 1960s 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 wont 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. Hes 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.