Leonardo DiCaprio Fashion and Film Showcase 2019 - A Hand Tailored Suit

Leonardo DiCaprio Fashion and Film Showcase 2019

In his 44 years, Leonardo DiCaprio has starred in over fifty films. Over the last 25 years, Leo’s style has evolved with his film choices. Let’s take a look at a Leonardo DiCaprio Fashion and Film showcase.

The 1990s

In 1993, Leo starred in What’s Eating Gilbert Grape with Johnny Depp. He was nominated for both a Golden Globe and an Academy Award for his performance. In typical 90s fashion, Johnny and Leo appeared at the premiere together with Leo wearing navy trousers, an oversized black button-up ribbed sweatshirt, a brown belt, a beaded necklace, and an oversized jacket. He styled his hair in typical long style, parted in the middle. Depp wore a black suit with pointed 70s lapels on his white button-up shirt.

Here is another Leo 90s look with a black pointed lapel button-up and a bright fuchsia suit.


He even appeared alongside future co-star Brad Pitt for the 1995 premiere of Pitt’s film Seven. Brad wore a suit and Leo opted for a black t-shirt and brown leather jacket.


Baz Lurhman’s Romeo + Juliet abridged modernisation of Shakespeare’s iconic play in 1996 catapulted Leo to stardom. The film’s costumes were downplayed, colourful and modern.


But it was in 1997 when Titanic came out that he was a household name, playing penniless Jack Dawson opposite another newcomer, Kate Winslett. Leo smartened up his red carpet look by wearing an old-fashioned cut tuxedo in black with a black bow tie.

Years later, the two have appeared on the red carpet together several times.


In later years, Leo has been known both as an outstanding actor and as a man who famously dated supermodels.


Gangs of New York (2002)

In this film, Leo plays a young Irish immigrant, Amsterdam Vallon, released from prison, hoping to avenge his father’s death against a powerful anti-immigrant gang leader, William Cutting, set in 1860s New York. For the film premiere, Leo’s look was sharp in a classic black suit, white button-up, and black tie, seen with his famous co-star Cameron Diaz.


Catch Me If You Can (2002)

Catch Me If You Can is a film about Frank Abagnale, Jr., a master of deception and forger who successfully claimed he was a doctor, lawyer, and a co-pilot for a major airline, all under the age of 18. Then, he became a successful bank robber. In the film, Tom Hanks plays an FBI Agent Carl Hanratty, working to catch Frank and bring him in. At the film premieres, Leo kept things simple with a classic navy suit or a classic black suit, usually with a monochrome look and slicked-back hair.


The Departed (2006)

The Departed is about a South Boston cop, Billy Costigan (played by Leo) going undercover to infiltrate the organisation of gang chief Frank Costello (played by Jack Nicholson). As Billy gains the mobster’s trust, a career criminal, Colin Sullivan (played by Matt Damon) simultaneously infiltrates the police department. Both organisations realise there’s a rat amongst them and Billy and Colin need to figure out who that person is to save their own lives. For this premier, Leo upped his style game with more vibrant ties and better cut suits.


Inception (2010)

In Inception, Leo played Dom Cobb, a thief who can enter people’s dreams and steal their secrets in their subconscious. He’s lost everything he loves by using his skill and selling out to corporate espionage. He has a last chance of redemption to plant an idea but with an enemy chasing him at every junction. For this premiere, Leo went more smart-casual, losing the ties and using a contrasting jacket and trouser combinations.


The Great Gatsby (2013)

The 2013 film based on the famous F. Scott Fitzgerald novel saw people copying Leo’s glam 1920s looks from the film. Leo plays the iconic Jay Gatsby, trying to win over a long-lost love, the socialite Daisy, the narrator Nick’s cousin.

Leo kept up his classic tuxedo look for the premiers. 


The Revenant (2015)

In this film, Leo played 1820s frontiersman Hugh Glass in which he’s brutally attacked by a bear and must fight for his life whilst also hunting down the man who left him for dead.

For this film, Leo won his first Academy Award for Best Actor, despite it being his eleventh nomination.

Leo’s premiere looks saw him in dapper, well-fitted suits.


Once Upon a Time in Hollywood (2019)

For Leo’s latest film, his style hasn’t disappointed. His looks have been more fashionable suits, with and without ties. Well-cut and fitted, his style has certainly evolved since those early 90s years.

This new film is about the Manson Murders and is the latest Tarantino film.


Do you want to dress like Leo?

If you want to be as stylish as Leo, A Hand Tailored Suit has you covered. We create custom looks to make you look and feel like a celebrity. Want to be the best dressed person in the boardroom or the ballroom? Contact our tailoring team today. Here’s how to get in touch.

Need more fashion inspiration?

We publish blogs each week to keep you abreast of the latest in tailoring, celebrity style, and fashion-forward looks. Check out some of our most recent posts by visiting our blog page.