Leonardo DiCaprio may regret his first date outfit because he's never worn it again

April 10, 2024

While promoting his new film, Killers of the Flower Moon, Leonardo DiCaprio has spoken about his fashion choices, especially when it comes to impressing the ladies on a first date.

Leonardo DiCaprio says that he regrets the outfit that he wore on his first-ever date. He regretted it so much he hadn’t worn one since!

Leonardo – accomplished actor and fashionista?

In an interview with Access Hollywood, the Titanic star, who just turned 49, talked about wearing turtlenecks as part of the costume for his new film and didn’t have many good things to say about the clothing item.

The celebrity looked bemused as the interviewer said that he and his co-star, Lily Gladstone, looked “great” in turtlenecks and, after a bit of awkward silence, he was asked: “You big on turtlenecks, Leonardo?” he responded: “Am I big on turtlenecks? Not really.”

He then opened up about wearing one on his first date. The Hollywood actor explained: “I did wear one on my first date … I haven’t worn one since.” He then says that he got it from Mervyns.

The legend of the turtleneck on Leonardo DiCaprio’s first date

This isn’t the first time he’s spoken about the date or the turtleneck.

In a 1995 interview with Movieline Magazine, a 20-year-old Leo went into further detail about his date and clothes.

He said (per Cheatsheet): “I went out with this girl named Cessi, this littler Spanish beautiful girl. I was in the eighth grade. We had this beautiful relationship over the phone all summer, she was away, and we were so close and so bonded, and we’d tell each other everything. And then she came home, and we went out to the movies for the first time, and, oh God, I wanted it to be so perfect.

“So I put on my light blue turtleneck, which I thought was cool at the time. It was a turtleneck I bought from Kmart or something. When I saw Cessi, I was petrified and I couldn’t even look her in the eye or speak to her.”

It seems Leo has had more luck with dating in Hollywood since…

Martin Scorsese calls Leo “very interesting”

Leo has worked with Martin Scorsese numerous times, including on Gangs of New York and The Wolf of Wall Street. It’s no wonder why when reading what the 81-year-old has said about him.

The movie director explained in an interview with Deadline: “What’s great about Leo, and it’s why we work together so often, is he goes there. He goes to these weird places that are so difficult and convoluted, and through the convolution, somehow there’s a clarity that we reach.”

“And usually it’s in the expression, in his face, in his eyes. I’ve always told him this. He’s a natural film actor. I could shoot a close-up of him, he could be thinking of nothing, and I could intercut anything with it, and people will say, ‘Oh, he’s reacting to such and such’. It’s the Kuleshov experiment. You could do that with him.”

The Kuleshov effect is when audiences can interpret more meaning from a sequence of shots rather than just a single one.

“There’s something in his face that the camera locks into, in his eyes. The slightest movement, we know it. Thelma [Schoonmaker], editing his footage with me over the years, often goes, ‘Look at this. Look at the eye movement here. I think we should keep it.’ It’s very interesting what goes on behind the eyes. It’s all there.”