50 Handsome Classic Mens Hairstyles | MenHairstylist.com Men Hairstylist

50 Handsome Classic Mens Hairstyles

The last couple of years have been full to the brim with trends such as the man bun, the top knot, man braids and perfectly shaved undercuts. However, there are still a few classic mens hairstyles that just transcend decades and style standards. They are the ones that have been working for almost a hundred years, and we know why. They make every man who wears them look good!

That’s why we’ve compiled a selection of the best and most handsome classic mens hairstyles. Scroll to the bottom and find the one that inspires you most.

1. Dirty Blonde Classic Mens Hairstyles

We begin with a sweet side part, a little wind swept and thoroughly good-looking. It’s what all of us think about when we hear the idea ‘classic haircut.’ Here’s a tip – use some extra gel or hair wax on your comb to get that watery look.

2. The Brad Pitt

There are a lot of Hollywood celebrities who love classic mens hairstyles and Brad is only the first one on our list. The classic cut with a side part perfectly mirrors his prominent and chiseled jaw, bringing him closer to perfection.

3. Salt and Pepper Classis Mens Hairstyles

Whoever said that men age like wine was completely right. They might have also said they age like fine Italian prosciutto because salt and pepper on them works absolutely like magic. Don’t be afraid and embrace the changes you are going through!

4. The David Beckham

When he was younger, Becks was famous for his soccer skills and for trying out every single haircut known to man and beast. Nowadays, he has settled for classic mens hairstyles and happier we could not be.

5. Frat House Classic Mens Hairstyles

There are Ivy League haircuts, Harvard haircuts, boarding school haircuts, which we will also cover in this article, by the way, and then there are frat house hairstyles. You can do them in style as well, without losing an ounce of dignity while chugging that beer.

6. The Henry Cavill

Superman himself could not have missed from the classic mens hairstyles list. Henry Cavill is a classically handsome man who benefits from this type of haircut. He has wavy hair which he loves to wear in a well-trimmed comb over.

7. The Zac Efron

Isn’t it wonderful when you get to see such a teen in what is clearly a manly haircut? This dapper take on the classic mens hairstyles brings out Zac Efron’s baby blue eyes as well as his beautiful, angular face.

8. Messy Pompadour Classic Mens Hairstyles

If you’re in love with pompadours, you’re also in luck. You can combine them with classic mens hairstyles and the result will be stunning. Slick back the hair for formal occasions or let it fall where it may for a messy do.

9. The Matt Bomer

Matt Bomer is, without a shred of a doubt, a true style icon. The good news is that you can now copy his classic mens hairstyles ideas, if you want. His gorgeous dark wavy locks need just a touch of hairspray and he’s out the door!

10. The Leonardo DiCaprio

In the past years, Leo has turned from the teenage heartthrob we saw in ‘Titanic’ and ‘Romeo + Juliet’ to the elegant and handsome man he is today. Evidently, his classic mens hairstyles have played a huge part in that transformation.

11. The Pierce Brosnan

The man who played James Bond had to be high-class and sophisticated. And we all know Pierce Brosnan is all that. He wears his hair in a demure pompadour, slicked back, with just a bit of wax in it, for added support.

12. The Jake Gyllenhaal

When it comes to classic mens hairstyles, Jake Gyllenhaal came over to the classy side as well. He left behind his more youthful years when he used to wear spikes and opted for a windswept comb over and a full on, thick beard.

13. The Ryan Reynolds

When you’re married to beauty queen Blake Lively, you do everything in your power to keep up, right? Apparently, this is what Ryan Reynolds thought when he adopted his classic mens hairstyles. Now he looks dashing and debonair.

14. The Jamie Dornan

Who better to advocate classic mens hairstyles than Christian Grey himself? Whether you are a fan of the books or not, you still have to admit that Jamie Dornan is a very handsome guy who knows a thing or two about seducing the ladies.

15. Fiery Classic Mens Hairstyles

One thing we encourage you to do as part of your routine into adopting a classic hairstyle is to go all natural. Even if that means white hair or keeping your original hair color. It’s all about being confident in your own skin!

16. Hipster Classic Mens Hairstyles

In case you ever wondered what Harry Potter would look like with a hipster hairstyle and tattoos, this is your answer. We especially like the hair color, which is a light tan blonde, as well as the classic waves.

17. Sandy Blonde Classic Mens Hairstyles

And speaking of blonde hair, if you have been blessed with this natural hair color, why not use it to your advantage? A head of hair and a full-on beard in this beautiful shade will work wonders on your appearance.

18. High School Classic Mens Hairstyles

Classic haircuts are so popular and versatile they even have a version for teenage boys that will not age them at all. Instead, they will look cool and dapper, especially if they learn how to style and accessorize it properly.

19. The George Clooney

Is there anyone in Hollywood who embodies the idea of a classically stylish and handsome man better than George Clooney? If you agree with us, then he should become your hairstyle inspiration. Add a little Clooney to your daily life!

20. The Hugh Grant

British actor and 90s heartbreaker Hugh Grant has a different take on classic mens hairstyles. The haircut that made him famous was a medium sized one, very wavy and with quite a lot of volume. He wore it slicked back over his head.

21. The Chris Evans

Captain America himself is another famous classic figure who needed a hairstyle to match. Actor Chris Evans obliged and turned to a nice, little Ivy League cut with a side part and a comb over, complete with a nicely trimmed beard.

22. The Dan Stevens

If Dan Stevens was handsome enough to play a Disney prince, you can trust him for some styling advice. In real life, the actor loves classic mens hairstyles, keeping his natural chestnut hair parted to one side in wavy, textured layers.

23. The Ryan Gosling

The world fell in love with Ryan Gosling in ‘The Notebook.’ Since then, Mr. Gosling has turned to classic mens hairstyles as well, becoming one of the most adored actors in Hollywood, thanks to his chiseled good looks.

24. Boarding School Classic Mens Hairstyles

If you love the British boarding school boy look, one way to achieve it from a styling point of view is by turning to classic mens hairstyles. Discuss the option with your stylist and take into account the shape of your face and the color of your hair.

25. Minimalist Classic Mens Hairstyles

A mid-sized pompadour can easily turn into what we call classic mens hairstyles if you know how to style it correctly. The undercut here is very important as it will give you that clean and elegant look you need to pull this off.

26. Curly Classic Mens Hairstyles

This, in technical terms, would be another take on the Hugh Grant type of classic mens hairstyles, only a lot slicker and more modern. You will need a lot of good quality hair care products if you want to pull off this look.

27. Side Part Classic Mens Hairstyles

The most basic type of a classic haircut is this one. All you need to do is get a medium sized cut, part your hair on one side, and use a wide comb to go through it. Add some hair wax to keep it all in place and you’ve got the hairstyle of your dreams!

28. The Tom Hardy

If there’s one thing that Tom Hardy loves when it comes to hair, that’s gel. His take on classic mens hairstyles is a slight messier version of what we’ve seen so far, all bathed in a lot of hair gel. Hey, it works for him!

29. Wavy Classic Mens Hairstyles

If you have a thick head of hair, one way of embracing it would be by growing it out to a medium length and then wearing it in handsome and classic waves. You can use some hairspray for this, as it will keep them in place and out of your eyes.

30. Classic Mens Hairstyles with a Combover

How would you look if you just returned from a ride in your convertible with the top down? This is what this hairstyle is all about. You need to look all devil may care, handsome and windswept as you run your fingers through your hair and steal girls’ hearts.

31. The Channing Tatum

Not even when he’s donning classic mens hairstyles can Channing Tatum let go of his signature spikes. We love it because he mixes the old and the new in this boyish yet handsome look we cannot wait but copy.

32. The Don Draper

Even though we know perfectly well it’s actor John Hamm, we still cannot help but see Don Draper when we look at him. He was absolutely exemplary in embodying that 50s classic picture-perfect man.

33. The Harvard Hard Part

Although Harvard is a hard part in itself because it’s an Ivy League College, that’s not what we’re talking about. Ask your stylist to give you a hard part using his razor and then an Ivy haircut. Then you’ll have a Harvard hard part.

harvard hard part classic mens hairstyles


34. Beach Side Classic Mens Hairstyles

A lazy day at the beach doesn’t mean you can skimp on the way you look. However, that’s the beauty of a classic cut. You can style it very easily with just a little bit of hair wax and make it look like you just came back from the barber.

35. The Orlando Bloom

How can a pirate in a bowtie look good you ask? Classic mens hairstyles is the answer. He usually wears his naturally curly hair in a jaw length cut. But on the red carpet he goes for a slicker appearance and we couldn’t love him more.

36. The Clark Gable

Here is a timeless example of classic mens hairstyles. Clark Gable set the trend with his raven colored 30s finger waves and pencil moustache as Rhett Butler in ‘Gone with the Wind.’ He became a style icon for the ages.

37. The Prince William

Having to obey a rather strict dress and style code, Prince William of Great Britain evidently is a great fan of classic mens hairstyles. He is naturally blonde and wears his hair in wavy comb overs that highlight his blue eyes.

38. The Chris Hemsworth

He has had many hairstyles over the years, including extensions, for the movie ‘Thor’, a man bun, and a top knot. But we love him best when he decides to go for classic mens hairstyles, as they go perfectly with his rugged good looks.

39. The Benedict Cumberbatch

Even though he is not considered to be traditionally handsome, actor Benedict Cumberbatch is one of the most physically appreciated men in the world and has even gone so far as to win the title of the sexiest man. Copy his look now!

You may also like – 50 Cool Slick Back Haircut Ideas

40. The Tom Hiddleston

You cannot possibly talk about British classic mens hairstyles and not mention Hiddleston. Hearts swoon all over the place when he walks in. With rumored girlfriends such as Jessica Chastain and Taylor Swift, Hiddles knows where it’s at!

41. Messy Classic Mens Hairstyles

One misconception about classic mens hairstyles is that they always have to be perfect. That might have been the case in the past but you have to bring these haircuts in the present and you also have to make them your own.

42. Rugged Classic Mens Hairstyles

Another stereotype about a classic haircut or style, for that matter is that you always have to look pristine. In fact, you can look as rugged or messy as you want. What matters is the attitude of elegance and confidence that you exude.

43. Fingers Waves and Curly

Classic mens hairstyles are versatile enough to allow you to even combine two haircuts and still get the desired effect. This is a traditional cut that combines 20s and 30s finger waves with natural curly hair.

44. The John Krasinski

Even though the world fell in love with him as the goofy and giggly Jim Halpert on the massive hit TV series ‘The Office,’ John Krasinski is actually a dapper and elegant man in real life. In other words, he knows all about classic mens hairstyles.

45. The Eddie Redmayne

We have all learned by now that Redmayne is an absolute chameleon when it comes to both acting and his looks. The best part? He looks good in everything. Just look how dapper and fierce he looks in his three-piece suit and side part!

46. The Eric Bana

Few men in Hollywood can do elegance and manly grace better than actor Eric Bana. His ruggedness doesn’t chip away one bit at his sense of style. He wears his naturally curly hair short and perfectly waxed and styled.

47. The Luke Evans

The world took notice of Luke Evans in his roles in ‘Dracula Untold’ and ‘The Hobbit.’ But it wasn’t until his portrayal as Gaston in ‘Beauty and the Beast’ that we really fell in love with his sense of fashion and style. Luke Evans is truly one to watch in years to come!

48. The Tom Selleck

Whether you know and love him as Magnum P.I or as Monica’s biggest heartbreak, Richard, on ‘Friends,’ Tom Selleck is truly an advocate of classic mens hairstyles. Do you know what he’s even more famous for than his hair? You’ve guessed it! His moustache.

49. The Dapper Gentleman Classic Mens Hairstyles

A good hairstyle has to be paired with the right clothes and accessories so that it can give you the look you want. Our advice here is that you invest in a few high-quality suits, the proper accessories, such as sunglasses, watches, and jewelry and you start to learn how to put them all together in the correct fashion.

50. The Matthew Goode

It just seems that Britain is filled with classically handsome actors, doesn’t it? Matthew Goode is definitely one of them, especially with a hair like that. His dark chocolate brown hair highlights his baby blue eyes. He usually wears it in simple wind-swept waves across his head, paired with his favorite hipster sunglasses.


This is our selection of the best and most handsome classic mens hairstyles. From Hollywood A-listers to Ivy League haircuts, we gathered all the ideas you need to inspire you to change your look for the better today! What do you think? Tell us in the comment section below!

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