45 Oscar Worthy Leonardo DiCaprio Hairstyles | MenHairstylist.com Men Hairstylist

45 Oscar Worthy Leonardo DiCaprio Hairstyles

He had to suffer the consequences of freezing water, he was mauled by a bear, had a huge party with tons of raucous guests back in the 1920s, and managed to scam about half the people in New York City. Still, his hair looked amazing through it all. We’re talking about Leonardo DiCaprio, of course, and his plethora of outstanding roles which helped him channel his styling game. These are 45 Oscar worthy Leonardo DiCaprio hairstyles.

1. The Shaggy Teenage Leonardo DiCaprio Hairstyles

Even though he has been blonde for most of his life, his hairstyle has changed quite a bit as the actor progressed through the years. When he was a teenager, he used to sport an age-very appropriate, shaggy and messy haircut.

2. The Gelled 90s Look

Leo was always a fan of medium hairstyles, never having cut his hair short, unless a role in a movie required him to do so. Here he is back in the 90s sporting the famous ‘wet look’ which could be obtained by using copious amounts of hair gel.

3. Blowout Leonardo DiCaprio Hairstyles

Although a traditional blowout typically includes a temple fade, we can let it slide, because this is Leonardo DiCaprio we’re talking about, and consider this one-of-a-king hairstyle of his a blowout as well.

4. Middle Part Leonardo DiCaprio Hairstyles

As a rule of thumb for young Leo, if it was shaggy, he liked it. He used to wear his hair in a medium cut all the time and then mess it around a bit using his hands giving it that free and fresh feel we all know.

5. The Volumized Comb Over

However, as he grew older and matured, Leo decided to go for more elegant hairstyles that represented his personality better now that he wasn’t a teenager anymore. This volumized comb over is a perfect example of the transition from boyhood to man.

6. Leonardo DiCaprio Hairstyles with Spikes

The actor also went through a period in his life when he sported short, blonde hair with spikes. It was very brief as we’ve already established that he doesn’t like short haircuts. Still, he wore it so it’s important to mention it here, for your consideration.

7. 50s Leonardo DiCaprio Hairstyles

Here’s solid proof that Leo looks good in absolutely any hairstyle possible. This is a haircut inspired by the ones worn in the 50s. It’s very reminiscent of James Dean in Rebel without a Cause or John Travolta in Grease if you prefer musicals.

8. Mature Leonardo DiCaprio Hairstyles

Here is the Leo that we all know and love today. It’s quite a departure from all those ‘class clown’ teenage pictures of him with ruffled hairstyles we’ve seen so far. These days he likes to wear a side part with his slight widow’s peak showing at the front. Plus, he is no longer blonde.

9. The Man Bun and Beard

Leo also had quite an extensive period when he sported this grizzly look which included long hair slicked back into a low man bun and a very big and bushy beard. The overall look fell nothing short of a disguise.

10. The Great Gatsby Look

If you’re looking for hairstyling inspiration and your go-to source is Leonardo DiCaprio, then you need to delve into his many characters. They are all iconic and have signature looks which you can copy and wear in your day-to-day life.

11. Heavy Bangs Leonardo DiCaprio Hairstyles

Leo was also always big on bangs. He doesn’t sport them anymore now, but he used to heavily back in the 90s and 2000s. Here he is with a full-on set of heavy bangs that reach down to his eyebrows.

12. Messy Bangs Leonardo DiCaprio Hairstyles

Continuing on bangs, here is another take your can try for yourself. These are messy 90s bangs in a light blonde color which Leo used to love. It’s this look of carelessness, confidence, and always having fun that won him the title of a fun guy to be around.

13. Bottle Blonde Leonardo DiCaprio Hairstyles

Truth be told, Leo is not a natural blonde. He has chestnut brown hair which he used to dye blonde when he was younger so that it could highlight his baby blue eyes better. It worked like a charm and the ladies simply swooned when they saw him on the big screen.

14. Asymmetrical Bangs Leonardo DiCaprio Hairstyles

We’re back to the bangs business because they were a huge part of Leo’s styling life. These are his overly long, asymmetrical bangs which made him look a bit like a bad boy. Here are some more shaggy hairstyles for you to try out.

15. Pre-Teen Leonardo DiCaprio Hairstyles

Here’s a very young, almost childish Leo with a short, blonde comb over. Yes, he was wearing the comb over before it was even cool, and he was absolutely rocking it. This is what it means to be a real star and a trendsetter.

16. The Chestnut Brown Side Part

When he got older, Leo decided it was time to throw the blonde hair bleach to the bin and find a color closer to his natural one. He also completely changed his look and demeanor and forgot all about his mischievous youth. Leo looked like a character from Mad Men.

brown side part leonardo dicaprio hairstyles


17. The James Dean Look

People have always loved Leo for who he is, but there’s no way one cannot love him a bit more when he’s channeling other iconic figures in Hollywood. Here he is with a full-on James Dean look straight out of Rebel.

18. Parted Bangs Leonardo DiCaprio Hairstyles

Black tie events don’t mean that Leo didn’t bring his beloved bangs to the game. On the contrary. Back in the 90s, when he did a major red carpet event, he used to part his hair down the middle and use extra hair gel.

19. Bronde Leonardo DiCaprio Hairstyles

Going from blonde to dark brown after literally decades of being a blonde must not have been easy for the actor. Therefore, it was a process performed in stages, with him also going through a bronde phase for one of his movies.

20. Layered Leonardo DiCaprio Hairstyles

A layered hairstyle is perfect for men with thinning hair and, as hard to believe as that sounds, Leo is now one of those men. Receding hairlines and loss of hair are extremely common among men and a part of the life cycle.

21. The 90s Boyband Look

Back in the day, Leo really looked like he could be in a full-on boy band of the 90s considering his spiky, blonde, gelled hairstyle. He, of course, would be the talented, cute, and funny one, and the band would be called Leo’s Direction. Get it?

22. Wispy Bangs Leonardo DiCaprio Hairstyles

When we said Leonardo DiCaprio loves bangs, we weren’t kidding. Here’s yet another version of fringe that the actor used to wear when he was young. This time it’s long and wispy bangs. If you notice anything different that’s because, for once, he’s not wearing any hair gel.

23. The High and Tight Short Crop

Leave it to Leo to wear a hairstyle ahead of its time, like always. This is a high and tight relatively short haircut with a parting down the middle and the almighty bangs which by now we’ve come to learn that Leo loved more than anything.

24. Wavy Leonardo DiCaprio Hairstyles

Although his hair is naturally straight, Leo has been known to sport a wavy hairstyle now and then, mostly for different parts he has played in his movies. Here is one of those times where you can see the actor with a side part and wavy locks.

25. The Oscar Haircut

Leonardo DiCaprio is unofficialy the most famous person ever to win an Oscar. Millions of people all over the world believed that it was ridiculous for an actor of his caliber with iconic roles and performances such as his would simply not be given an Oscar by the Academy. So they went on a relentless campaign of mockery and meme marketing that lengthened over years about how Leo was never going to win. Until he finally did in 2016 for The Revenant.

26. Elegant Leonardo DiCaprio Hairstyles

Here’s a hairstyle to copy if you have to go to a special event such as a wedding, a party or your prom. You know you will look good because it is Leo approved.

27. Cool Leonardo DiCaprio Hairstyles

Do you remember when Zayn Malik had that incident with the strand of hair which fell on his forehead and the entire internet broke down? This is proof that Leo did it first and looked equally, if not even better than Zayn did.

28. Medium Leonardo DiCaprio Hairstyles

A medium and darker colored hairstyle makes Leo look a bit older and more serious. If this is the look you’re going for, you can try it out as well. It’s perfect for a casual style that doesn’t require a lot of maintenance.

29. Pompadour Leonardo DiCaprio Hairstyles

Yes, Leo had a pompadour as well before it was cool. In fact, he had a very early version of what we have now come to call a pompadour. He used to comb all his front hair back and use some volumizing mousse to give it extra body.

30. Headband Leonardo DiCaprio Hairstyles

Headbands are necessary when you have medium hair and long bangs. They are perfect for going to the gym as well as day-to-day activities when you simply cannot have your hair bothering you.

31. Artistic Leonardo DiCaprio Hairstyles

Here’s the actor in another one of his roles sporting a layered and vintage hairstyle. It’s reminiscent of men of the past centuries, a character which he plays so well and has done so throughout his career.

32. Leonardo DiCaprio Titanic Hairstyle

Even though he has brought to life arguably some of the most iconic characters in the history of cinematography as you are about to see in the following paragraphs, his role as Jack Dawson is still the one the entire planet recognizes most. Here is the side part, medium blonde haircut he wore in Titanic, and a still of the famous portrait scene.

33. The Romeo + Juliet Hairstyle

Leave it to director Baz Luhrman to create one of the most enduring images of Leonardo DiCaprio ever. This is the young actor in Romeo + Juliet wearing a Hawaiian shirt custom-made for the movie that was meant to represent the Montague spirit and which greatly appealed to millennials the world over.

34. The Django Unchained Hairstyle

We cannot possibly talk about Leonardo DiCaprio hairstyles without mentioning Django Unchained and his southerner wavy side part. He received critical acclaim for his portrayal as well as styling acclaim for the way he looked.

35. The Revenant Hairstyle

We’ve already seen Leo’s hairstyle on the night he won his Oscar. Now it’s time to see his haircut in the movie he won the Oscar for. We’re talking about The Revenant, of course, a role for which he grew his own hair and beard to make it look as realistic as possible.

36. The Shutter Island Hairstyle

Another favorite of the public is Shutter Island. In this one, Leo sported a very short hairstyle with a side part and a layered and feathery comb over. He also wore a five o’clock shadow that matched his retro haircut.

37. The Aviator Haircut

In this critically acclaimed movie, Leonardo was impersonating Howard Hughes. Therefore, he also had to sport the super short and gelled haircut, complete with a hard part and, you’ve guessed it, aviator sunglasses.

38. The Man in the Iron Mask Hairstyle

One of his roles when he was younger was in The Man in the Iron Mask where he played both King Louis XIV of France and his twin brother whom he was keeping locked up and with his face hidden away in an iron mask.

39. The Gangs of New York Hairstyle

No Leonardo DiCaprio hairstyles list would be complete without his Gangs of New York look. His hair was long, natural in color and very shaggy looking, bordering on the unkempt, exactly as you would expect his character to behave.

40.  The Catch Me If You Can Haircut

We’re back to comb overs in this movie. Leo plays real-life Frank Abagnale, Jr. who managed to pretend and work as a lawyer, doctor, and co-pilot on an airline before he turned 18. Tom Hanks plays FBI agent Carl Hanratty, who chases the teenager as he schemes his way into millions of dollars.

41. The Blood Diamond Hairstyle

Here is a very short and cropped look for Leo, which he sported for the highly acclaimed movie Blood Diamond. The hairstyle is layered and features a set of baby bangs cut very closely to the hairline.

42. The Departed Haircut

As far as Leonardo DiCaprio hairstyles go, The Departed one might be the easiest to copy and wear in your day-to-day life. It’s a slightly longer version of the famous buzz cut to which Leo has added a few spikes at the front and just a touch of his famous blonde hair.

43. The Revolutionary Road Hairstyle

After the historic success of Titanic, Leo teamed up with the fabulous Kate Winslet once more in 2008 for the harrowing drama Revolutionary Road. The amazing thing is that the two actors have remained friends in real life as well after all these years.

44. The Wolf of Wall Street Hairstyle

Here’s an instance where you can see Leo’s receding hairline as well as his widow’s peak. For this role, he had to die his hair a lot darker than he has ever worn it and get a massive amount of tanning done.

45. Childhood Leonardo DiCaprio Hairstyles

We’ll end with this more than cute photo of baby Leo hugging a teddy. You can see that even back then he was sporting the same haircut that made him famous and an actual heartthrob later on.


Leonardo DiCaprio has definitely had his fair share of Oscar worthy roles and movies throughout his career. But we also believe he has had some moments worthy of an Academy award when it comes to styling as well. Who can forget the iconic, quintessential 90s hairstyle in Romeo + Juliet, his blonde teenage heartthrob look from Titanic or his fierce demeanor in Django Unchained? Write to us in the comment section below and let us know which one of these Leonardo DiCaprio hairstyles was your favorite!

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