1. Diddy
For most, Diddy, or Puff Daddy as most older folks know him, burst on the scene around 1992. Since then, his trailblazing style has been followed by everyone. Over the years, Diddy's style has evolved and he has shown that men and women can have styles that reach both the urban, modern youth as well as the executive crowd, as pictured above. Confident in his own sense of style, Diddy created the Sean John clothing line to punctuate his sartorial savviness. Whether walking the streets of Harlem, styling on the red carpet or in the boardroom, Diddy's look is always impeccable.
2. David Beckham
Viewed as a metrosexual by many, David Beckham knows exactly who he is and what his style is. The term "comfortable in one's skin" is often thrown around loosely, but it really is applicable to Beckham. He knows what clothes and styles show him in the best light. What's more, this guy truly knows how to wear ink. His body is adorned with tattoos that are of real significance, rather than of the latest fad. His best accessory, however, may be that hot wife of his, Posh Spice. She'd make any man look dashing.
3. Brad Pitt
Mr. Pitt is another man with a great piece of arm candy, but that's not the only thing that sets him apart. Brad looks great dressed down, as pictured above, or dressed up on the red carpet with his hair slicked back, a la 1950s style. He knows which accessories to use and isn't at all afraid to make statements and take risks with his hair. To put it simply, he makes looking great look effortless.
4. George Clooney
As far as a style icon, George Clooney is one great example of one. He has been said to own one Giorgio Armani tuxedo and worn it exclusively on the red carpet, so much so that the designer sent him a new one. The lesson here is to adopt a signature style and stick to it. Mr. Clooney is always very classic and basic in his fashion choices, but when you exude debonair presence, you don't need much else.
5. Usher Raymond
Usher has gone from hip-hop to haute couture. High fashion isn't just for women and Usher has proven it. He's a style chameleon in that he can go from jeans and sneakers to a nice fitting Dsquared2 suit. He teaches us that it's important to have versatility in our style. While maintaining a signature style, it should encompass many different facets. Usher also dresses age appropriate, there is nothing worse than an older man dressing too young or a young man dressing like his grandfather.
6. Will Smith
While once a goofy teenager in the late 1980s, Will Smith has evolved into a really stylish adult and shows that style doesn't stop when you cross the 40 year old threshhold. Taking control of his body, hair and wardrobe, Will personifies a comfort level and inner strength that most men can only dream to achieve. This Philadelphia native selects age-appropriate clothing no matter the situation.
7. Tom Ford
Tom Ford, the man who breathed life back into Gucci brings us to our next lesson, sex appeal. Mr. Ford is often seen in an immaculately tailored suit and a white crisp shirt unbuttoned to reveal a bit of chest. While this look isn't for everyone, it's important to feel good in what you wear and also feel attractive. Proper fit and color choice are key in this.
8. Justin Timberlake
Justin Timberlake has evolved quite a bit from his days with N'Sync. He's dropped his curly fro' for a sleeker cut and the boy band uniform of baggy and pseudo-urban in favor of jeans that fit and blazers from his William Rast line. This lesson is the most important, evolution in what you wear. Over time you should be like Justin and adapt your clothing and accessories (ties, shoes, cufflinks, etc…) to fit your lifestyle and attitude.
9. Tom Brady
While many professional atheletes shun dressing debonair, Tom Brady embraces it wholeheartedly. Brady, who dresses in classic style, drapes himself in Ermenegildo Zegna suits while gracing the covers of publications like GQ, Sports Illustrated, Esquire and Boston, to name a few. When he's not busy winning superbowls and conducting interviews, Brady takes care of the son he had with actress and ex-girlfriend Bridget Moynahan and rolls around town with current girlfriend and super model Gisele Bundchen. It's good to be the king!
10. Terrence Howard
Terrence Howard is a personal style icon of mine. A while back on the red-carpet, he wore two brooches on his lapel and was the talk of the red carpet. I had a formal event to attend and found a brooch to adorn my velvet blazer lapel, it killed! The lesson with Terrence is to take trends and make them work for you. While my brooch wasn't Tiffany's or Chopard, it worked great with the outfit I wore. Don't be afraid to take risks because they may work for you.
Honorable Mentions
It is sad, but you have to draw the line somewhere. Here are three more men that really know how fashion, fit and form can speak volumes when done properly:
Jamie Foxx
Back in the late 80s/early 90s, Jamie was like most men during that time, pretty unfashionable. Since then, a few multi-platinum albums and Oscars later, Jamie is one of the best dressed men in Hollywood. Jamie is a risk taker, often wearing bold blazers and adorning his outfits with flashy pocket squares.
Howie Mandel
I know what you're thinking, "Howie Mandel?" Yes, friends, Howie Mandel. I'm not sure exactly when his transformation occured, but since he has been on the hit game show, Deal or No Deal, Howie has been "puttin' it down!" This man is impeccably dressed with finely tailored suits in every episode, often matching the hot ladies carrying the steel briefcases. Howie often wears slim-fitting, modern cut suits and shirts from designers such as Joseph Abboud, Prada, Gucci, Dolce and Gabbana, Paul Smith and Ted Baker.
Andre 3000
Don't try this at home! Andre Benjamin, a member of the rap group Outkast, has honed his style over the past 15 or so years. Sometimes wearing outlandish outfits, sometimes wearing more mainstream ensembles like the one pictured above, Andre 3000 is definitely a big risk taker. Not many men would be caught dead in lime green feather boas, but he's not at all deterred. He's comfortable with his style. I'm not sure if he tries to shock or if he genuinely loves everything he wears, but one thing is certain: He is bold, he has his finger on the latest trends and he understands fashion as it relates to the modern man.
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