Leonardo Di Caprio Most Stylish Films

 As we near the release of the much anticipated Scorsese's Killers of the Flower Moon, I thought I'd take a retroactive look at some of the key style moments of one of the film stars Leonardo Di Caprio.

Inception

Arguably one of the most stylish films of Leo's was Christopher Nolan's Inception. The arthouse blockbuster has a timeless legacy and the suits were especially made for the movie by Costume Designer Jeffrey Kurland. The late Costume Menswear writer Christopher Laverty spoke about interviewing Kurland remarking,

He clearly loves doing male-dressed suiting. I think he has a really good eye. His clothes don't date that much.

The Wolf of Wall Street

Di Caprio is one of those actors who has never bothered to attain a muscular physique for any role. Yet has always managed to look statuesque in the right suiting. He tends to wear a fuller cut suit alternating between tie and sans tie depending on the event. He is a brand ambassador for TAG HEUER, which explains why he was contractually obliged to launch a gold plated TAG HEUER, posing as a Rolex, across the office floor in The Wolf of Wall Street. An interesting article on Leo's watch collection can be found on Horologistico.

Whilst the suits in The Wolf of Wall Street were designed to reflect the fashions of the 80s, the casual elements have remained unblemished by the scrutiny of time. The yacht outfit for example where Di Caprio's character Jordan Belfort, is still discussed and highly sought after even today. Menswear commentator Jon Shanahan commented on that outfit as,

Yeah, that yacht outfit is the iconic look from this film. I mean that is the one that everybody remembers. It looks great. The white polo I mean, that’s just a classic, white polo that anybody can pull off.

The Great Gatsby

With the advent of Peaky Blinders, the 1920s style trends have made a huge renaissance. The high rise trousers, the newsboy caps and especially braces. Di Caprio also had a hand in this style push when he starred in the divisive The Great Gatsby (2013). According to the book Fashion in Film, Master Tailor Martin Greenfield in his early eighties coordinated all the production for DiCaprio's and Tobey Maguire's suits. In total the company [ Brooks Brothers ] supplied 500 ensembles for the cast and extras made up of 1700 including shoes ties and shirts.

Once Upon a Time in Hollywood

Di Caprio also shows his versatility as a style icon when he stars in Once Upon a Time in Hollywood. A nostalgic-reverent take on the style and societal vicissitudes of the 60's and 70's. According to the show notes on From Tailors With Love,

Leonardo Di Caprio (who played Rick Dalton) had up to 30 costume changes throughout. There were some Tarantino-isms in this film with regards to the Hawaiian shirts; Tim Roth in Pulp Fiction, Christian Slater in True Romance.

Love affair with Giorgio Armani

In I.D's Leonardo Di Caprio Style evolution article, the writer bookends the discussion with Di Caprio's Oscar winning Giorgio Armani Tuxedo that he wore when collecting Best Actor for The Revenant in 2016. In fact Di Caprio has enjoyed a long collaboration with Armani having worn his suitings on various red carpets, for a variety of award ceremonies. In an article for GQ magazine Armani himself remarks on clothing Di Caprio,

I have dressed him on many occasions, on the red carpet but also on set. I like the relaxed and natural way in which he wears my clothes, his nonchalant style: he has a spontaneous and masculine allure, on set or off, whether he is wearing formalwear or a T-shirt with jeans."

In conclusion Di Caprio is arguably one of the best actors of our generation. He looks as effortless buttoned up as he does in his casuals. He is not a flashy dresser, yet typically New York downtown in his down time. But when called upon to get scrubbed up, he can do it with a flick of a switch.