45 Groovy Old School Haircuts | MenHairstylist.com Men Hairstylist

45 Groovy Old School Haircuts

Fashion and style are cyclical, we all know that. Right now, for example, we are living in a full-on 90s meets 50s revival where the entire male population seems to be divided into two teams as far as hairstyles go. They are either wearing some version of the 90s heartthrob haircut or a pompadour. Still, are there more hairstyles from decades long ago that may yet make a comeback? Check out this list of old school haircuts and find out!

1. The Classic Pompadour

The pompadour haircut was invented in the 1700s for Madame de Pompadour, a mistress of Louis the XIVth. Up until the 1940s and 50s, it was a hairstyle for women, but prominent figures such as Elvis made it into a completely masculine one.

2. The Jelly Roll Haircut

This one is called the Jelly Roll and, just like the pompadour, it too was popular among men during the ‘40s and ’50. As far as old school haircuts go, it belongs to the famous ‘greaser’ era called thusly because of the amount of grease or oil it took to style their hair.

3. The Rockability Pompadour

Here’s another version of pompadour from those years. These haircuts emerged during the 50s because young men rebelled against the very conformist and scrubbed image teenagers were supposed to have during the ‘30s and beginning of the 40s.

4. The Gelled Pompadour

This was the haircut of the rebel youth of the 50s, who didn’t like to conform to the norm. They also wore white T-shirts only, blue jeans with a straight leg and, of course, the now immensely famous leather jacket which they helped popularize.

5. Curly Rock’n’Roll Old School Haircuts

Greaser boys with old school haircuts such as the pompadour or duck tails were also considered to be somewhat dangerous because they didn’t play by the rules. However, they also received their fair share of flack for being vain and spending a lot of time doing their hair with grease every day and always having a comb with them.

6. The Clark Gable

As far as old school haircuts go, if we go back further in time, we can find the exact thing that greaser boys were trying to rebel against. This is the clean-cut look of the 30s, as expressed so handsomely by legendary actor Clark Gable.

7.  Rebellious Old School Haircuts

It’s a bit funny how we think that being a rebel started with punk in the 70s when this type of theatrical jelly roll was a form of rebelling as well. They were going against the conformist ideals of the 1920s and 30s who taught boys that they shouldn’t spend too much time on their looks.

8. Old School Haircuts with Finger Waves

Speaking of the 1920s, here’s a haircut from way back then. These are the famous finger waves that both men and women used to wear. Since then, men have dropped them, and only women still wear them for special events such as weddings and costume parties.

9. The Douglas Fairbanks

During the 1910s and 20s, Douglas Fairbanks was nicknamed ‘the King of Hollywood’ thanks to his many movies and celebrity status. He also hosted the first ever Oscars back in 1929. You can see him pictured here in a typical hairstyle of the era.

10. College Old School Haircuts

Today’s Ivy League haircut is a descendant or a version of this old school hairstyle that most young men used to wear in the 1920s, 30s, and 40s when they enrolled. It’s a medium and wavy cut with a true sense of bohemian style to it.

11. The James Dean

It was impossible to create a list of old school haircuts and not mention one of the most famous and iconic looks in history. James Dean wore the greaser haircut himself. In fact, he was one of its most ardent supporters.

12. The Ronald Reagan

This is former US President Ronald Reagan when he was young. As you can see, he’s sporting the most fashionable haircut of the 30s and 40s for young men who wanted to keep it nice and clean and not rebel against the system.

13. The Clint Eastwood

This iconic Hollywood actor is wearing a pompadour in this picture with a very feathery and layered finish to it. Always a fashionable man as his status as a major Hollywood actor asked him to be, Clint Eastwood was a hit with the ladies.

14. High and Tight Old School Haircuts

Jumping all the way to the 70s and 80s, we get to see this little gem that has, unfortunately, all but disappeared today. This is called the high and tight, for obvious reasons. You can also notice how one side is higher than the other.

15. Asymmetrical Old School Haircuts

The same two decades brought us this nugget of inspiration that was considered the epitome of cool back then. If you also paired it with large shoulder pads and some golden bling to match, there was no one better than you.

16. High Top Old School Haircuts

There’s no need to explain why this hairstyle is called a ‘high top.’ The idea here is to grow your hair out but cut it in the shape of a tube or a funnel so that it becomes as high as possible and you annoy the people in front of you at the cinema. We joke, of course. This is an iconic haircut.

HIGH TOP old school haircuts


17. The Box Top

The box top is a shorter version of the high top, but more polished around the edges. You literally need to make it look as if you were wearing a box on your head. A box made of hair. We’ll let you try and find the reasons why.

18. The Mullet

We have seen a lot of old school haircuts and put even more of them on this list. But the undeniable king of all haircuts is the mullet. This hairstyle is also called the ‘business in the front, party in the back,’ and it’s absolutely legendary.

19. Creative Old School Haircuts

There are old school haircuts that routinely make their way back to us such as the pompadour or the Mohawk. And then there are some which don’t. Perhaps because they look like this. They are surely fun for a throwback, but maybe keep them in the yearbook?

20. The Bowl Haircut

You may be surprised to learn this, but the bowl haircut is actually making a very silent and stealthy comeback. It has been seen on red carpets and at fashion shows all over the world. You can try it too!

21. Punk Old School Haircuts

Another iconic haircut has its roots deep in the 70s and it came as another bout of rebelliousness from the American and English youths. They were rebelling against the conformity of the decades before them and used their hair and clothes to show it.

22. 60s Hippie Old School Haircuts

Speaking of the 60s, here’s a stereotype hippie with long hair and the now mega-famous headband, as well as flamboyant clothes and round glasses. The flower power revolution was a hit, and everyone was striving for peace.

23. The Peacock Revolution

Let’s stay in the 60s a little while longer for some more old school haircuts. Another interesting thing happened to men during that decade. They went through a massive change which Esquire magazine called ‘The Peacock Revolution.’

24. 60s Old School Haircuts

In other words, men started wearing very bright colors and flaring prints to show that they were opposed to the earlier decades which had been very drab for men. In this way, they resembled peacocks.

25. 60s Old School Haircuts with Bangs

You can now see the Peacock Revolution being brought to life by artists the likes of Harry Styles who wears the same type of bright patterns and flaring suits with theatrical jewelry, sequins, and as much glitter as he can possibly fit on his clothes.

26. 70s Old School Haircuts with Afros

Moving on to the 70s, we can find these fine gentlemen wearing afros. This is a real picture from the 70s. Notice the soft, unisex clothing with paisley patterns, open almost all the way to the front and the flaring pants, a reminiscence of the 60s taken to the extreme.

27. Medium Length Old School Haircuts

The 70s continued the 60s taste for the peacock revolution. Men did not stop wearing bright colors or crazy combinations. It was the beginning of decades long of trying to erase the starch differences between genders and fighting for equality.

28. Old School Haircuts with Mustache

This is the famous 70s mustache. Even though men have dropped it a long time ago, it’s still incredibly famous mainly because it has become a stereotype associated with that decade and depicted in movies and TV shows.

29. The Mick Jagger 70s Old School Haircuts

We could not have possibly talked about the 70s and not mention Mick Jagger. His feathery, layered, and almost feminine haircut was iconic. In fact, it still is. Even today, when people see this hairstyle they immediately think of the Rolling Stones rockstar.

30. Modern Old School Haircuts

This is what a version of 70s haircuts looks like today. This is a model on the runway for the Gucci Fall 2016 show. He’s sporting the same type of layered and soft haircut we’ve seen so far in original photos from the decades plus a myriad of accessories that put us in mind of the 70s.

31. The Danny Masterson

Another familiar face you might recognize is Danny Masterson or Steven Hyde from That 70s Show. Evidently, seeing as the show was based in that decade, his curly hair was styled to look like he actually lived then.

32. The David Bowie

This is a picture of singer and actor David Bowie back in 1979. His ginger-blonde hair is cut short both on the sides and in the back, but he has a longer front which is very feathery and light. This is a perfect solution for men with fine hair such as his.

33. Glam Rock Old School Haircuts

Welcome to the age of glam rock! Yes, we’re down to the 80s now, and we have been welcomed here by big hair, big voices, and even bigger attitudes. The 80s saw the rise of the glam rocker with outrageous outfits and the biggest hair in the industry.

34. 80s George Michael Haircut

Who doesn’t remember this George Michael hairstyle? He used to wear it when he was still part of Wham!, his boy band. It’s a feminine and blown up style that also has a set of gorgeous blonde highlights in the front.

35. 80s Prom Old School Haircuts

Prom was a big deal in the 80s, and most of the stereotypical, albeit comical, imagery we have now comes from that decade. There were the theatrical suits with the frothy shirts as well as, of course, the stylish mullets.

36. Cool 80s Old School Haircuts

But there was also a way for you to be cool back in the 80s. If you were young and hip, you had to sport this medium-length comb-over haircut, complete with a baggy, silk shirt and a snake print tie. Cool is a relative term.

37. The Miami Vice Style

Another style that made absolute legend in pop culture is what we now call the Miami Vice look. It was popularized by the stars of the eponymous TV show and consisted of a sleek, white shirt plus a baggy coat, usually in a very bright color and with the sleeves upturned.

38. The Sylvester Stallone

It’s probably safe to say that not all styling decisions that were made in the 80s were good ones. This throwback picture of actor Sylvester Stallone is a good example. He’s wearing a set of very long and highly gelled curls with equally curly bangs and he does not look happy about it!

39. The Axl Rose

From a styling mistake to an iconic look that will live through the ages. Axl Rose of the Guns’n’Roses was very much part of the Glam Rock era but decided to go against the big curly hair trend that swept the likes of Bon Jovi, Steven Tyler, Ozzy Osbourne, Brian May, Alice Cooper, and so on. Instead, he kept his gorgeous redhead locks sleek and shiny.

40. The George Clooney

This may come as a surprise seeing as George Clooney is the epitome of elegance and good-taste now, but in the 80s he actually sported a shaggy mullet. We cannot blame him because everyone did, and he wanted to be cool.

41. The Tom Selleck

Our younger readers might know him as Richard, Monica’s boyfriend from Friends. But Tom Selleck rose to great fame as Magnum P.I. on his own show in the 80s. He used to wear lots of hoola shirts, a curly 80s haircut, and his uber-famous mustache that Chandler envied so much.

42. The Brad Pitt

Here’s actor Brad Pitt in the 80s with the same type of teenagery feathery haircut. He was blonde and very good looking back then as well, evidently destined for great things in Hollywood.

43. The Matt LeBlanc

There is no one better to represent the beginning of the 90s decade in hairstyles than Matt LeBlanc. He broke many hearts on Friends with his good looks, a gelled haircut, and that one line that made history – ‘How’ you doin’?’

44. The Leonardo DiCaprio

Another Hollywood sweetie that wore the typical 90s haircut was Leonardo DiCaprio. His version was blonde, and it highlighted his baby blue eyes. It was his preferred hairstyle for a very long time.

45. The Hugh Grant

However, nobody embodies the 90s heartthrob look better than Hugh Grant himself. The actor made movie history with his British-casual-elegant style that simply swept women off their feet in films such as Notting Hill and Four Weddings and a Funeral.


Old school haircuts are a fascinating subject for anyone even remotely interested in fashion and style. They are also a trove of ideas for those seeking to look to decades already passed and finding there the spark that ignited revolutions and sent cultural messages all over the world. The Greasers of the 50s, the Peacocks of the 60s, the Punks of the 70s, the Glam Rockers of the 80s, and the heartthrobs of the 90s will forever be our inspiration.

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