The Stylish Jerk’s Role Models

Hopefully you have read through the Into section and have completed the “Find Your Style Series”. If so, then you should be ready to tackle whatever style you want too. When creating your style, it is important to find role models that you can learn from. Everyone is different, I don’t expect everyone to agree on what I find is stylish. The Intro should provide a blueprint to help you create a style, and this article should help you create a blueprint to find your role models. My other material will be based on a style that is similar to these other gentlemen. If you like my role models, then you should enjoy the other content I have in the style section.

I chose my role models based on my own perceptions. Most of us have dress for different occasions in our lives. Sometimes we have to dress up, and other times it is more appropriate to be casual. So I found my role models for each different occasion, and I divided them into different categories.

Categories are Best Class, Best Casual, Best-All-Around

Best Class

(George Clooney)

In an age where American men would rather wear a blazer/jean combo to every work function, Clooney has stuck with always wearing a fully tailored suit. When the trend was to wear lighter colored suits and flashy colors, Clooney stuck with simplicity. A no-nonsense haircut, an elegant watch, and a dark shirt/navy suit combo. Clooney has brought back a gentlemen like essence that we have not seen since the days of Humphrey Bograt and Carey Grant.

(Joseph Gordon Levitt)

Levitt went from the nerdy guy in 3rd Rock From The Sun to action hero in Inception/The Dark Knight Rises. Part of this shift I believe is how he pulled of the waistcoat in Inception. Levitt has shown how to properly wear a fitted waistcoat in any casual and formal situation and look like a badass doing it.

(John Slattery a.k.a Roger Sterling)

Everyone and their mom talks about the style of Don Draper, but few talk about the style of character Roger Sterling. In my opinion, Roger Sterling pulls of the best three piece suit that I have seen in television and cinema. Also, the ability to look like the owner of the building instead of a hipster while wearing big framed glasses is an added touch.

(Ed Westwick)

Yes, I am using the dude from the Gossip Girl. Yes I understand he looks like the frat guy who stole your girlfriend, dumped her, and then went on to work at Wall Street even though he had a lower GPA. Either way, Westwick is one of the best I have seen that wears suit with a modern look (skinnier tie) while still following the same principles that men have followed while wearing suits for the past fifty years.

(Tom Brady and Kobe Bryant)

I put these two into the same category, because I have similar feelings for both of them. I believe there are some of the most egotistical players in any sport, but you cannot deny, when it comes to suits, there are one of the best dressed. Kobe is known for wearing classy Armani suits, neutral shirts, and bold necktie to complement it. Brady is known for wearing dark gray suits, plaid dress shirts, and topping it off with a neutral tie.


Jay-Z is man that went from poor to wealthy. A man who went from selling “rocks” to now being one of the wealthiest men in the world. Even with his wealth, Jay-Z still has glimpses of his roots in how he wears his suits. Classic tailoring, with subtle and dark color colors. A suit that that represents business, success, and respect. One that would fit right into the Al Capone era.

Best Casual

(Kid Cudi)

An artist known just as much for his music as well as his taste in style. Kid Cudi still wears chains, air jordans, aviator glasses, and snapbacks that are popular with hip-hop culture. But, combines them with timeless pieces such as the leather jacket and the denim jacket. Also the fit of his clothing is never to baggy or to skinny. Combine all these factors, and Kid Cudi is one of the best when it comes to casual clothing.

(Michael Fassbender)

Fassebender has a style that is not flashy at all. He is known for only wearing the simple essential in men’s clothing: jackets, neutral t-shirts, jeans, and sunglasses. But it works. Fassbender shows that all men really need to do look good is stay in really good shape, wear clothes that fit, and wear men’s clothing that is timeless and not trendy.

(Tinie Tempah)

This hip-hop artist is not really big in America, but he soon will be.  Tinie Tempah has won many style contest including, GQ Britain. Tempah is known for wearing the basic staples and than taking risk with those staples. Wearing ripped-camo shorts with a denim jackets and a pair of air jordans is an example.

(Phillip Crangi)

Phillip Crangi is a man many of you probably never heard of. He is a fashion designer and a known trendsetter for jewelry. Usually I do not follow trendsetters, but this guy has a personal that is badass. He is known for wearing steel, iron, and gold jewelry combined with his main essentials.

(Donald Glover aka Childish Gambino/Troy)

Every once in awhile when I go out I want to have a little fun.Donald Glover’s style is unique in the sense that it is fun. He combines jackets and cardigans with ironic t-shirts, nerd glasses, and bowties. His style may not always be taken seriously by some, but as a nerd who grew up playing Playstation I enjoy it.

Best All Around

(Dan Trepanier aka The Style Blogger)

This guy is one my biggest inspirations for style. He is a college athlete who won Esquire’s Best Dressed Man in America. After that his popularity took of. Dan combines upscale elegance with casual wear better than anyone I have seen. Check out his site “”, if you don’t believe he is one of the best dressers in America he probably would at least make your top ten.

(Lebron James)

I am still in disagreement about how he handled the situation in Cleveland, but I really can’t say anything bad against him now. He is arguably the best player in basketball, he is now a champion, and to top it off he is arguably one the best dressed men in America.  He can pull of the laid-back casual artist look with ease and then later wear one of the best power suits I have ever laid eyes on. As long as King James, keeps his ego intact he is a player to admire on and off the court.

(Kanye West)

Kanye West is known to many for his antics rather than his achievements. His new relationship with Kim Kardashian and the Taylor Swift fiasco are a few examples. What a lot of people do not mention is how Kanye, by himself, changed the popular trend of wearing baggy jeans and oversized jerseys. Kanye came into the scene wearing denim jackets/preppy attire for his casual wear and tailored suits for the red carpet when it was not popular to do so. Kanye has changed a whole younger generation to adopt to a more gentlemen like style, and for that he has my thanks.

(Daniel Craig)

It was only 6-7 years ago when critics doubted that Daniel Craig could do James Bond justice. Well now Daniel Craig is in his third bond movie, Skyfall, and now critics are calling him the best bond since Sean Connery. Instead of letting the new fame get to his head, Craig seems to live a more understated lifestyle. Even his clothes have a certain gentlemen like demeanor that was more popular in the past. Everything he wears is mostly men essentials: cardigans, jackets, suits, henleys, and dress shoes. That is it. He does not wear any flashy graphic tees or break the creative mold in any way, but his clothes are tailored to perfection. It’s the little details that make Daniel Craig one of the best dressed men in Hollywood right now.

(Ryan Gosling)

It was a tough decision to chose the MVP for this site, but I went with Ryan Gosling. Here is why. Approximately four years and half year ago Ryan Gosling was fired from the movie “The Lovely Bones” for gaining to much weight and was replaced by Mark Walkberg. He said himself that for awhile he was, “fat and unemployed”. Three years his career completely changed. His movie “Blue Valentine” was getting Oscar attention and he completely switched his style up.

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