The Evolution of Leonardo DiCaprio as a Fashion Icon

Photo by Quinn Buffing on Unsplash

Leonardo DiCaprio has now been on our screens for over 30 years. During this time, he has taken on everything Hollywood had to offer, and always risen to the task. From teen heartthrob fame to academy award winner, he has thrived in every type of possible role. Throughout it, he has always maintained his position as a fashion icon. Below, we give our top three Leonardo DiCaprio outfits from his movies.

Romeo + Juliet

Before Romeo and Juliet, DiCaprio had several roles in which he built a fledgling reputation for himself. His first role had been in the direct-to-video Critters 3, but the movies seemed to get much better after this. He was handpicked by Robert De Niro to star in This Boy’s Life. In The Quick and the Dead, Sony Pictures had been against his casting. So sure was Sharon Stone of his success, that she offered to pay his salary. With these heavy hitters behind him, it was only a matter of time before his first big commercial break came along.

Romeo + Juliet, directed by Baz Luhrmann, was a modern remake of the Shakespeare classic. The original dialogue and plot remained, but the whole movie had a semi-modern update in Luhrmann’s unique style. That included some very on-point fashion choices.

The most iconic outfit of the whole movie is DiCaprio’s Hawaiian shirt selection. Large sleeves and lapels are a nineties look that has recently crept right back into fashion. Summing up a golden era of MTV cool, they ranged from Japanese floral prints to pop art patterns. Oddly, it would be a look director would return to throughout their whole career. Combined with loose-fit jeans, it is a much easier look to pull off than the suit of armour.


Titanic was the role that cemented DiCaprio as a household name. It was the highest-grossing movie of all time, bringing in $2.1 billion at the box office alone. A fictional account of a young couple who meet onboard the ill-fated Titanic maiden voyage, it is their love story as the ship meets its untimely demise.

So successful was the movie that it is still hugely popular today. A range of merchandise and licensing products still bring in revenue. These are even as varied as Titanic-themed online slots – ranks very highly when looking at online slot reviews. Though all of this is in addition to many licenses for clothing and other products, along with the enduring appeal of its hugely successful soundtrack.

Not only was it a huge success, but it also set off a manic fandom around DiCaprio that became known as ‚Leo Mania‘. Fans mobbed him in the streets, in a phenomenon DiCaprio himself would be rather embarrassed about later in his career.

Regarding fashion, the actor had a much more muted wardrobe than the rest of his movie. Gone were the nineties fashions and in came linen shirts and bracers. This low-class casual approach fit with the divide played upon in the movie and was ahead of the trend that would appear at the end of the decade.

The Great Gatsby

It would be impossible to do F. Scott Fitzgerald’s novel justice without having everyone at the height of Belle Epoch fashion at all times. The movie arrived at a time when the roaring twenties were coming back into vogue, and plenty of fashion brands were aching to donate clothing and items to the movie. The move brought back DiCaprio with Baz Luhrmann, who he had worked with on Romeo + Juliet.

The most iconic outfit in the whole movie is not that extravagant at all. Gatsby himself sports a well-tailored white suit, with an ochre waistcoat under a clashing blue shirt. It makes an excellent contrast to the excessive outfits of the others character in the movie. Created with costume designer Catherine Martin, they are a lesson in how cut and colour can make something so simple and so cool.