Some haircuts simply never go out of style.
The prime example is some old-school haircuts that we still see men wearing today.
Some of them have been with us for centuries while others are coming back.
But, how to know which is which?
How to determine which old-school haircuts are cool?
You are probably thinking to yourself that you might choose poorly and end up being laughed at for sporting a hairstyle that nobody wears anymore.
Actually, the possibility of that is very real.
But not if you know where to look.
To shorten the elimination process, we found dozens of suitable old-school hairstyles for men that are trending currently.
With our help, you will be able to choose a suitable one for you in no time.
Table Of Contents
65 Most Popular Types of Old School Haircuts
The classic Pompadour haircut is one of the most popular hairstyles for men of all time. It was made famous by the King of Rock himself, Elvis Presley but was initially intended for women. The hairdo originates way back in the 1700s as Madame de Pompadour wore it, the mistress of Louis the XIVth. But men in the 40s and 50s started wearing it and completely revolutionized the style.
The Pompadour haircut is characterized by heavy portions of hair on the top, combing back and away from the face. The sides are significantly shorter and contrast the longer top quite well. Today, it is viewed as a trendy style perfect for successful men. It goes well for those with an oval, round, or triangle-shaped face.
The secret in making this hairstyle work is by blow-drying your hair back as you comb it and utilizing a lot of the world’s best pomade for men to keep it steady.
Old Fashioned Slicked Back Hair
The old-fashioned slicked-back hair is a barbershop favorite. It is a trendy look, but it is very easy to create and maintain. You need to use a strong hair product and brush your hair back, and you are done as simply as that.
This style is versatile because it works both on an undercut and on longer hair. But we do agree that it looks much better when a guy slicks back some longer follicles. Just think of Johnny Depp and how he looked in his movie Cry Baby.
However, this hairstyle is notoriously hard to keep together on some thick hair. It works better for guys with fine hair. It is also ideal for those with a triangle face or those with a longer face type.
The rebel without a cause, James Dean, sported a retro quiff, which is everything there is to know to learn the nature of this hairstyle. It is a natural and casual look with a lot of volume on the top of your head. Even though some quiff hairdos come with a neater look, we like the unkempt one far better.
What makes this style work is that men from all walks of life can wear it. Politicians, athletes, newscasters, literally anyone. But it goes much better on those with either a triangle, oval, square, or heart-shaped face.
The key to this haircut is to blow dry your hair away from your face but then slant it to one side. It is not your classic side part haircut style because it has some characteristics. But be sure to use a lot of hair sprays to keep it together after you set everything in its place.
Traditional Haircut on the Sides
When you think of a traditional haircut on the sides, your mind has to immediately race to Ziggy Stardust, our favorite Starman, or Major Tom. We are, of course, talking about David Bowie. Even though Bowie went through a number of phases and styles changes, think of him in his most natural, laid-back, and traditional form, and you will understand what this haircut is all about.
It does not require much to create this style. You have to grow your hair a bit, get a simple haircut, and comb it on the sides. You shouldn’t cut the hair too short; it needs volume. It works best on fair-haired fellows and particularly well on those with a boyish charm.
What makes this hairstyle popular is that maintenance is very easy. You will not even need to use any products to keep it together. But you do have to comb your hair every day to make it work.
Old-Fashioned Comb-Over Hairstyle
Many people tend to mix the old-fashioned comb-over with a side part. But the two are two very distinct hairstyles altogether. But what connects them is that they both invoke an intelligent, serious, and dapper look.
Short tapered sides characterize a vintage comb-over, usually cut with scissors, and a top style that can be short or medium cut. Also, the top doesn’t go without a pomade. Some modern versions of the comb-over include a high, mid, or even low fade on the sides with optional tapering that fades into the skin.
The old-fashioned comb-over is a versatile look that fits various styles and is trendy for every occasion.
Don’t be confused with the wording gangster haircut, as it is less thrilling than you might think. Old school gangsters usually wore styles much similar to modern businessmen as it helped them to blend in. But the Hollywoodisation of the look has born a few very amusing and trendy styles that have made their way into the mainstream today.
The classic gangster haircut is similar to a gentleman’s and includes a classy and clean cut with short sides and a medium-length top. You can add a slick back or a side part to make things interesting. Or you can copy Arthur Shelby or even Tommy Shelby for a modern gangster look.
Old Fashioned Short Haircuts
Old school hairstyles are characterized mainly by keeping the top longer and the sides shorter. But some old-fashioned ones involve maintaining short things altogether. People mostly wear a retro style that has a short top fringe.
Since people used to wear hats back in the day, the messy fringe kept under the hat was good. People may not be wearing hats so often, but they undoubtedly enjoy the style. This one is perfect for casual, everyday activities and it does not require a lot of maintenance and certainly does not need excess usage of a premium hair tonic. But you still should try and keep it neat.
Jelly Roll Rockabilly Rebel
A Jelly Roll is another old-school haircut that appeared among men during the 40s and 50s. It was worn mainly by Rockabilly and Greaser guys and was known as a rebellious rock and roll look.
You should know about this old-school haircut because it requires a lot of grease to keep in place. You might think that this is not something that guys do these days, but it is where you are wrong. If you want to know about pomades vs wax vs gel vs clay, you should ask a greaser guy about it.
That said, the haircut is hard to maintain and requires regular do-overs, even while you are wearing it. But if you don’t mind the grease, you will enjoy the Jelly Roll very much.
Retro Finger Waves
Retro finger waves are a haircut that goes even further than the Jelly Rolls and the Pompadour. It dates back to the 1920s and was worn by both men and women at the time. Men stopped wearing finger waves at one point but have since made a comeback as one of the more peculiar old-school haircuts.
Guys with wavy or curly hair will be able to create and pull off this hairstyle much easier. The hair on the top has to be kept long and brushed on the side with the waves on the very top. It is most popular among very young and handsome fellows nowadays.
Old Fashioned Bad Boy Haircut
A bad boy is a bad boy, so this kind of hairstyle hasn’t changed so much even in decades. Short and tapered sides, medium to long top, a stubble beard. This is what a bad boy look is all about. It does not seem overly complicated, and it isn’t, but it does leave a massive impression.
This style has similar characteristics to the gentlemen’s style but is more free-flowing and comes with more natural volume. The free-spirited nature of the hairdo is what makes it perfect for bad boys. But you can’t have this style without a beard and even a bushy and thick one will look good even though stubble would be a better choice.
Classic Old Fashioned Cowboy Hairstyle
A classic cowboy hairstyle incorporates shorts sides combined with slicked back or brushed back hair. The top is, of course, kept much longer than the sides. Instead of a beard, this style requires some handlebar mustaches to make it work.
Back in the day, the old-fashioned cowboy-style symbolized masculinity and represented the rebellious nature of cowboys. Today, we don’t have a lot of rebels, but it still emphasizes the masculine nature of the wearer.
It is a style that macho men will enjoy and will wear with confidence.
What Is an Old School Haircut
An old-school style means taking a step back a decade or two and starting wearing something that the cool guys of the days prior used to model. It does not mean that you will have the same hair set as your grandfather, but something in the line of what Elvis Presley used to wear or a Rock n Roll haircut that Danny Zuko from Grease had.
Classic short haircut styles for modern gentlemen are still popular and will never go out of style. But you can’t deny the fact that old-school styles are making a comeback. Just look at the gangster family epic Peaky Blinders and the hair that the Shelby family and their adversaries wear. Now look around you and chances are that you will see a few of those worn by young and old all over.
With so many historic epic shows and movies showing exactly how things used to look back then, it prompted many haircuts to make a comeback. And rightfully, they should as they have something to show. A mix of a classic and a little bit of modern has always been able to spark something new and exciting and it’s what we call evolution.
Therefore, old-school haircuts are not a step back. But a step forward in style and hair care.
How to Do It
Step 1 – Find a good barber
First of all, you have to find a good barber. Before doing that, you have to know how to identify your desired unprofessional hairstyle. You don’t want to end up with an unsuitable set of hair that will make you regret your choice.
We propose having a frank talk with your barber first and get their opinion about it. Alternatively, you can look for a good one online or ask your friends. Then you can start making plans about which hairstyle to try out.
Step 2 – Pick according to your face type
The pick should be made based on your face type. Choosing an old-school hairstyle that does not go with the shape of your face will ruin everything. Once you double down on a haircut, decide whether you want some facial hair or not. Things work splendidly if you can perform a cool-looking mustache or an impressive beard with the hair.
But you can’t have the hair without the clothing. Complete your entire look by choosing some appropriate garments that will go with the haircut and possibly the stache.
How to Style It Perfectly
If you know how to cut your high-top fade like a barber, then you are halfway there. But styling your hair as appropriately as possible will take some dedication. First of all, it depends on the style you have chosen as some require more while others are going to need less care.
Step 1 – Use Vaseline hair tonic
Regular maintenance is needed, depending on the old school style, whether it is with long or short care. Once you leave the barber, you will need to style the hair daily. You can easily work it up into your morning routine before going to work. You may only require some vaseline hair tonic or a whole bunch of stuff; it all depends on the style you are going with.
Step 2 – Groom hair along with the beard
If your old-school hairstyle comes with a beard, that also means more work. Grooming the hair and facial hair will prompt you to sacrifice some more time in daily grooms. But it will all be worth it in the end.
Don’t be shy to ask your barber for beard and hair tips. These are going to be of valuable help as you maintain your style. A good barber knows best and will always tell you what to use or what not to use for a specific style. Old school haircuts may be a bit more tricky to maintain than some standard ones but come with an excellent reward of you looking as unique as possible.
How do traditional men cut their hair?
You are rarely going to find a person who cuts their hair. Men traditionally have a barber that they stick by and visit often. If you can find a good one, you shouldn’t waste your time looking for a different one and stick to what you know works.
What is the most popular old-fashioned hairstyle for men?
Even though men sport a few popular old-fashioned hairstyles these days, the most popular ones have to be the comb-over and the slick back.
Which hairstyles will never get old?
It is hard to say which haircuts never go out of style; the traditional haircut on the side is the one that has stood the test of time the most.
Old school haircuts are not only making a comeback, but they are already here and they are here to stay. More and more men are enjoying the compliments they are getting with the way they are carrying these old-fashioned hairdos. A great style will never go away no matter how old it is and the ones mentioned above are certainly some that will be around for a while.