Men’s Style Revival

It’s fashion season around these parts, in case you had not noticed: fashion week is upon us in Bryant Park in New York, awards season is here which means an abundance of designer outfits that will be worn one time and then donated to charity, Michelle Obama and her designer, Jason Wu, are getting a ton of press for their garments. But one thing late last week caught my attention.

In advance of their latest issue, GQ announced online their choices for the Ten Most Stylish Men in America. The complete list and slideshow can be found here, but below is a quick rundown of the men who made the list:

Justin Timberlake – entertainer – named most stylish man in America
Mark Ronson – DJ, producer
Alexi Lubomirski – photographer
Andre Balazs – hotelier
Kanye West – pop musician, aspiring designer
Sid Mashburn – haberdasher, Southern Gentleman
T.I. – M.C.
Glenn O’Brien – GQ’s Style Guy
Jason Schwartzman – actor, indie rocker
Ed Ruscha – artist, LA icon

I don’t by any means think that any of these men are not stylish. In fact, I applaud GQ for not doing a safe list with the same old names like George Clooney, Johnny Depp, et al. At least these are some men we may not have heard of before, and we are allowed to peer into the world of some new(er) faces.

But this list got me thinking about stylish men in America – more specifically, who I feel are the most stylish men in the history of this country. So while I have put plenty of thought into this subject before, never before have I put my thoughts down on paper (read: hard drive) as to my picks.

So I present to you, sticking with the theme GQ established, my most stylish men in the history of America. Presented in no particular order.

Robert Redford

This is one of my favorite pictures of all time and is a paragon of timeless style at work. Despite the fact that this picture was taken about 30 years ago, look at the outfit: the slim jeans, the tweed jacket, the aviators, the boots – you could lift this right off of him and place it on someone today and it would work. Maybe we can leave the mustache behind, however.

Redford has always been one of the best of pulling off an outfit no matter what the time frame or circumstance. He seems to effortlessly accept what must be worn and pull it off with confidence.

One of the most underrated stylish movies, in my opinion, is Spy Game, with Redford and Brad Pitt. Redford’s style in the movie spans the Vietnam war, Germany and Eastern Europe in the 80’s, and 1990’s Washington DC. Watch it – the style journey within is amazing.

John F. Kennedy

Imagine an entire country following a trend based on one day of one man’s life. Well that is exactly what happened after Kennedy’s inauguration in 1961. Kennedy braved a cold January day with no fedora or top hat, becoming what is believed to be the first president to do so. From that day forward, hats were no longer a staple in men’s wardrobes.

This day would eventually become just the first of many days that a country would look on this president as a style icon. Whether in his office, at home, sailing, or playing with the kids, his style was always impressive – some would say, presidential.

Dean Martin

Probably the swankiest member of the famed Rat Pack, Dean Martin was known for heavy drinking and always looking good. Martin was famous for always having three things at his disposal – a cigarette, his legendary charm and the best clothes he could find. Ruling an entire town such as Las Vegas required as much.

But he and his gang would always be linked with the eat-drink-and-be-merry lifestyle of the Wes Coast in the 50′s and early 60′s. The tragic assassination of the man listed above sent a country into turmoil and a once-invincible man into a career decline.

Tom Brady

A more modern addition to my personal list – this debonair quarterback went from relative unknown from Michigan to a Super Bowl-winning, MVP-dominating, model-dating, stylaholic.

It certainly doesn’t hurt to have the physique and body type that is of designers’ dreams, but whether in a post-game interview, on the cover of GQ, or walking around town delivering flowers on an injured foot, Brady exudes style. It’s almost like he tries, but knows he doesn’t need to try. There is an Italian saying known as sprezzatura, which essentially states that the confidence or nonchalance that one displays masks the effort it took to put work into something, therefore making that work look effortless itself.

That’s what I think of when I see Tom Brady.

George Clooney

OK, I know what I said about him above, but he has to be on the list. Immaculate suits, well-cut tuxedoes, his patented open-collar look, three Oceans movie that revived the appeal of men’s warm-climate fashion – Clooney has represented or reintroduced too many iconic styles to not be included. Plus he has a villa on Lake Como – what is more stylish than that?

And remember, Clooney has not only become well-known for his attire, but for other individual features as well. Who can forget his ER days when he seemingly single-handedly brought back into style the Caesar cut. Since that time, his hair styles have made men many times over pray for more salt-and-pepper in their locks.

Andre 3000

I don’t know for sure about this hunch I have – but I get this feeling that, when all is said and done, Andre 3000 (known for his time in Outkast) will be better known as a designer than a musician. Andre’s label, Benjamin Bixby, is inspired from pieces out of the 1930′s, and has recently earned him honors as one of the top new designers in America by GQ.

I guess you could describe his and his label’s style as hip-hop preppy, but you can get a better idea by just glancing at the picture above. A student of older generations, Andre draws on the experience and style of older generations he meets to inspire him in creating looks that transcend the time-gap and meld into modern, popular wear.

Cary Grant

Yes, Cary Grant was born in England, but he became a household name in America as a movie star – often named on many lists as the greatest movie star of all time. Grant, for the purposes of this list, is the oldest, the original, and the best. All definitions of style, suave and gentleman should start and end with him. In fact, it has been rumored that Ian Felming’s James Bond was based in part off of Cary Grant.

Again, what a truly incredible example of men’s clothing that could be lifted right off of this photograph and onto the gentleman of 2009 and no one would think twice about it – simply timeless. Notice the subtleties that are evident, but that don’t stand out on their own such as the simple cufflinks, the barely-showing pocket square, one button done on his jacket, etc.

Paul Newman

Wearing a pair of jeans and a white t-shirt was never a fashion statement until Paul Newman made it one. Always a man who kept things simple in fashion, perhaps the greatest thing we can learn from his style doesn’t have to be about clothes at all. Newman was a man who was comfortable in himself, and truthfully would have preferred just to spend most of his time like he is in the picture above. If a man is not comfortable with himself, it shows. It shows not only in clothes, but in attitude, in outlook and in lifestyle.

If you think of all the movies and appearances Newman ever made, you can probably not think of any one thing that stands out about the way that he looked or what he wore. The famous mustache and fedora in The Sting are about as close as you can get, I bet. Newman was never one to wow you with extravagance, but rather inspire you with simplicity and ease. He is man truly worth emulating.