The 10 Best Dressed Ugly Men…Who Get Women

Mark Twain, America’s most beloved author from the 19th century, really knew what he was talking about. He was an astute man with a sharp wit and incisive satirical flair, which led him to his place atop the apex of American literature. Works like The Adventures of Huckleberry Finn, which has been called the Great American Novel, and The Adventures of Tom Sawyer, have through history been extensively quoted and gained him a level of fame that found him cavorting with the likes of presidents, artists, industrialists and European royalty.

But more than all that, we want to pay homage to this man by highlighting what has become- in our minds at least- his most defining and lasting contribution to society, which he neatly summed up in 13 simple words:

“Clothes make the man. Naked people have little or no influence on society.”

We couldn’t agree more.

In honor of this great American novelist, we’d like to salute the man by showcasing in modern day pictographic terms, just how well and alive his words are today. By completely ignoring what some may believe to be his more significant works and contributions to society, we are taking a more realistic approach to our commemorative commentary on Mr. Twain.

Below you will find 10 men, who thanks to this Twainian credo, have been able to get the girl. OK, so maybe talent had a little something to do with their success. But let’s face it, all talent aside, these 10 men are downright ugly. Yet because they dress better than you or I ever will, they will always get the girl.

In no particular order:

1) Bill Maher – The perfect example as to how the equation, acerbic wit + super human intellect + great tailoring + troll-like face = seeing him with a new 21 year old hot girl every time he goes out.

2) Senator Daniel Patrick Moynihan – Though some may not be so familiar with our dapper Tortoise of the Senate (the similar reference to Ted Kennedy as “The Lion of the Senate” had less to do with looks, more to do with his tenacity of character), Senator Daniel Patrick Moynihan gets much of his legislation passed simply because his fellow senators find doing business with a tortoise in a bow tie as quite frankly the funniest thing on capitol hill.

3) Diddy – First off, having a fragrance called “I Am King” immediately puts you at a disadvantage. Quite frankly we hate you for that. But behind the beautiful suits and the fancy champagne stands a man who really is not all that good looking. Did you ever wonder why 97.5% of the time, Mr. Diddy is wearing sunglasses? No offense to our down-syndrome brethren, but he kinda looks like he has down syndrome, or what many less enlightened still refer to as a Mongoloid. I don’t want to be offensive, so let’s just leave it at we think Diddy looks like a Mongoloid sans-sunglasses.

4) President Franklin Delano Roosevelt – Before you go and get your tie all in a knot, we’re not saying that getting Eleanor Roosevelt necessarily qualifies FDR as having “gotten the women.” However, to her credit, the lady does have quite a pedigree, having been born into the elite New York high society known as the “swells” and therefore to some can be considered quite the “catch.” However, our standard response to any questions raised about her physical prowess will always steadfastly remain, “She’s a really nice woman.” But I digress. Back to FDR.

A true gentleman. A true man of class, intellect and compassion. He was the only president elected to more than two terms and led America through some of its toughest times- The Great Depression and WWII. Through it all, he always kept his tie knotted tight and high, his shirts pressed and fitted and his trusty pocket watch at his side. Despite this however, we still need to ask the man, Why the long face? Take a close look and FDR resembles Mac Tonight of McDonald’s fame circa 1986.

5) Fred Astaire – When a man of such stature as Fred Astaire conjures up images of Barney Fife of The Andy Griffith Show, you know you’re an ugly man. When a man such as Fred Astaire, who could dance, sing, act, choreograph the best shows Broadway or Hollywood ever saw, yet still looks like a caricature of himself in a bow tie, you know you’re an ugly man. We respect him too much to continue on with this blasphemy.

6) Jay-Z – The man lays down next to Beyonce every night- that automatically ups the expectations for the guy. Sure, he’s widely considered the best rapper alive. Sure, he’s since graduated from his laughable days of Roc-A-Wear to become a bonafide style icon in the world of music. And sure, maybe he has the charm, charisma, wit and confidence that would get a two-inch dick the girl. But the simple fact remains: Jay-Z is ugly. For one, his nose and mouth/lips take up at least 1/3 of face real estate. And secondly, if you squint just the right amount, Jay kinda begins to look like Mr. Magoo and Elmer Fudd wrapped up into one comical rapper.

7) Keith Richards – Mr. Richards has probably slept with more women than all of us combined. But for arguments sake, let’s say we plucked Keith Richards from this stylish LV ad and placed him in a line-up of average looking men say in a country like Micronesia (Any Pan-Asian-Pacific country will do). In this scenario, local women would be asked to pick the seed of their child. My bet is that he would be picked dead last. Sans fame and clothes, Keith Richards is just another junkie from Skid Row.

8 ) Thom Yorke – It took me a moment to decide if this was Thom Yorke or Clay Aiken. Once I was able to confirm that this was in fact Thom Yorke- Clay Aiken is ugly, terribly dressed, gets no women…or guys for that matter- I knew I had a quandary on my hands. All talent aside, Mr. Yorke does not even come close to trying to dress the part, look cool. get the girl, etc. Mr. Yorke essentially pulls off the aloof, talented, wunderkind role so well, it’s hard to bad mouth one that does not even try nor care in the least bit what we all say about him. It’s like that look that’s taken hold where one attempts to pull off a disheveled, controlled chaos, just-rolled-out-of-bed look yet in actuality it’s the most time-consuming contrived look of any out there…except Mr. Yorke’s seems to be genuine in nature. I suppose I can only say Thom Yorke looks like Clay Aiken, which should get my point across just fine.

9) Pete Doherty – Poster boy for “Say No To Drugs” Looks like your average street junky desperate for a fix and would put anything in his mouth to do so. However, the man looks so damn stylish doing it. We can’t help but think Mr. Doherty is the inspiration to The Chinese Man Inspiring Fashion in China.

10) Oscar Wilde – Our hero. By far the best dressed, erudite, sophisticated gentleman there ever was. We can’t verify if he actually got the girls, but we can verify that he was one of the top 10 ugliest men to ever walk the earth. And even his master tailor with his immaculately tailored suits couldn’t hide this fact. We still adore you Mr. Oscar Wilde.

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one suit, five looks

Dan Trepanier, named Esquire’s “Best Dressed Man in America” in 2009, has recently posted an enlightening piece on how to get the most of 1 (bold) suit, by breaking up the pieces for almost any occasion.

In his own words, “With the new age of cool, modern suits, however, we have so many more options than our power-suit-wearing predecessors. The jacket and the pants can be mixed and matched to create a look for just about any occasion.”

Take a look at his blog, The Style Blogger, and see how you can get away with wearing that one suit at just about any outing. CLICK HERE

The Monocle | Warby Parker Eyewear

Style blog, Get Kempt, put us onto a new piece from Warby Parker Eyewear that has us drooling more than when we lived in Shanghai and got massaged weekly byYu-Lin the blind masseuse (Yes, she is real. Losing the sense of sight, humans naturally adapt through the heightening of all other functioning senses. In this case, the sense of touch is enhanced to the point of being able to find knots and kinks you didn’t even know you had, but I digress).

Warby Parker Eyewear has recently included this monocle in their line sheet, a piece that has unfortunately faded from everyday conversations and even further from everyday wear. They’re calling this one the “Colonel Whiskey Tortoise.”

Hang this piece from your 3-button vest from a double albert chain, with compass fob opposite it, and you will easily become the envy of the entire room.

Sartorially Inclined | The Spread Collar

First of all, if you haven’t read the blog, Sartorially Inclined, then you need to bookmark that now. Sharply written, insightful commentary and impeccable taste, this blog is definitely one of those that make you a better man.

Secondly, there is a great article on shirt collars. We couldn’t agree more when they say, “…spread or cutaway collar seems like a real bold alternative right about now.”

Read more about how much the collar says about you  HERE.

Dean Chalkley's Exhibition 'The New Faces'

In 2010, it was believed Mods had long since left our streets. It was thought they were replaced by a lackluster generation of sweats and hoodie wearing individuals who put nothing above comfort.

Thankfully Dean Chalkley discovered this group of young mods at a club in London. Not only did they dress impecabbly, reminiscent of the sharp dressing men and women of the 50’s and 60’s, but they also carried a panache and moxy not seen since…well since the 50’s and 60’s.

In Chalkley’s own words: “These guys are the antithesis of the all too common don’t-give-a-fuck attitude of some young adults,” explains Chalkley. “They’re bright young folk who take a real pride in how they present themselves and they’re really into their music – mainly late 50s and early 60s rhythm and blues. They’re actually from varied backgrounds and different parts of the country – but their shared passion for music, dancing and looking sharp brings them together. And you should see them dance –they look good and they’ve got the moves!”

‘The New Faces’ exhibition opened this weekend at The Book Club on Leonard St. in London.

How To : Waterproof Your Shoes

In these wintry and often snow-laden days where slush and dirt mix to create an overwhelmingly messy and ruinous situation for your shoes, we felt like everyone should be aware of the little things you can do to help ensure your shoes stay good as gold all year long.

Our friends over at Art of Manliness have recently posted a great article on how to keep your shoes looking great even when trudging along the slushy boulevards of the winter season. Check it out HERE