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It’s no secret that I am absolutely obsessed with American actor and philanthropist, Leonardo DiCaprio. Everything from his convincing character portrayals and his passion for altruism has made him an iconic leading man in today’s society.

DiCaprio’s characters are memorable, not just because he made audiences believe that  these characters were authentic, but also because of the clothes. DiCaprio has had a tendency to play characters that mirror himself in “real life” – suave, confident and stylish.

Let’s look back on his five most stylish characters and collectively swoon at the perfection that is, Leonardo DiCaprio.


1.) “The Great Gatsby” (2013) – Jay Gatsby 

Jay Gatsby, the lovelorn party host from F. Scott Fitzgerald’s, The Great Gatsby, is everything but tacky. In the midst of the Roaring 20s, Gatsby has an apparent flare for the dramatic, ranging from his extravagant parties, wooing Daisy and his lavish wardrobe.

With his character living in an influential time in fashion history, Gatsby certainly does dress the part of a wealthy entrepreneur, his suits all tailored and in every colour you can imagine. He is far from tacky, however. As we saw in the scene where he is showing Daisy his shirts, he only buys the clothes from the most posh stores and keeps up with the latest trends.

And gents, here is one lesson you should learn from Gatsby – real men wear pink.


2.) “The Wolf of Wall Street” (2013) – Jordan Belfort 

Yes, his character in “The Wolf of Wall Street” was the walking definition of a greedy and materialistic jerk, but you can’t deny that all of his money bought him style.

Belfort was known to be flashy and proud of the material goods he had, but his style was just the right amount of flash. He often wore simple suits and added an accessory like a designer watch or sunglasses to complete the outfit.

His best outfit in the movie is without a doubt the all white ensemble worn on his yacht. If he didn’t pair this outfit with the rolex watch and the ray ban sunglasses and black and gold belt, this would be a boring outfit. Belfort was smart to pair his simple black and gold accessories to this outfit, as it indicates to audiences that he is rich without having to explicitly say or even show that he is. In this case, his simplicity gives just the right amount of flash.

Money may not buy you class, but it can buy you nice clothes.

9d9e74b021cc7ca17b4ada43aa5a2bdf3.) “Titanic” (1997) – Jack Dawson 

In the role that arguably made Leonardo DiCaprio a household name, he played the poor Jack Dawson who was a passenger on the ill-fated Titanic. Despite his limited means of income, Dawson certainly became a trendsetter in men’s fashion. Dawson’s preference of suspenders and plaid jackets are trends that are still popular today, proving that just because you are not filthy rich, you cannot be stylish.

Dawson also stuck to more basic colours like taupe, navy and browns, which are colours that every man should have in their wardrobe. They are colours that are flattering on every skin tone and they can be matched with anything else that you may have in your closet.

With these wardrobe choices in mind, you certainly will be compared to the artistic and  handsome Jack Dawson. Let’s just hope that you will have a much better fate than he did!


4.) “The Aviator” (2004) – Howard Hughes 

The life of Howard Hughes is one that has fascinated people for years, as his mind was a point of interest for scholars. While the film of his life certainly gives audiences an insight into his tortured mind, it also gives audiences a glimpse into his personal style.

An enigmatic and tortured figure, it’s refreshing to see how simplistic and clean Hughes’ style is throughout the film. Often wearing neutral coloured khakis paired with a blazer and tie, his aviator sunglasses have become iconic. This one accessory will make any outfit. Whether it is with a suit or a pair of jeans and a white shirt, the aviator sunglasses will definitely have people referencing the characterization of Howard Hughes.

4e8f7d268fe4bf3e0335caefbd2c6c025.) “Catch Me if You Can” (2002) – Frank Abagnale Jr.

In his portrayal of fraud criminal Frank Abagnale Jr., DiCaprio had to impersonate many career figures such as a doctor, pilot and a lawyer. With each role he had to impersonate, he was able to convince others that he was a trained professional in his selected field not only because of his use of professional jargon, but because he dressed the parts. And he did it with style.

Similar to Howard Hughes, Abagnale often wore the aviator sunglasses when he was impersonating a pilot. However, his all navy and gold suit was a throw to the pan-am era and is an eternally classic look.