27 Classic 1950s Men’s Hairstyles

Sleek and flattering, these 1950s men’s hairstyles are timeless choices for men who want a stylish look. As the coolest trends in the 50s, these classic men’s haircuts were influenced by American pop culture at the time, specifically the rebellious rock and roll revolution, growing jazz music scene and the so-called Golden Age of Hollywood. Some 1950’s haircuts were longer greaser and rockabilly styles like the pompadour and quiff that made a bold fashion statement, while short classy cuts like the comb over, slick back and flat top offered a clean, sophisticated look.

For throwback inspiration, we’ve compiled a list of the best 1950s hairstyles for men who want to experiment with a new look. If you want a retro vibe, these men’s haircuts from the 50s are some of the most recognizable and iconic styles that have stood the test of time.

Stylish 1950s Hairstyles For Men

Greaser Hairstyle

The greaser hairstyle is a retro look that was popular throughout the 50s and 60s. A greaser style generally uses a slick styling product to create a bad-boy look for young men. The style features short to medium-length hair on top that has been slicked back with some styling product like a pomade, wax, or gel. These days, it is common to pair this look with an undercut or a deep side part, but the traditional style was paired with a mid fade.

Classic Pompadour

The classic pompadour is a cool and handsome haircut for men who want a style that will stand out. The hair on top is left three or more inches long and swept upward away from the face, then held in place with strong hairspray, pomade, or gel. The sides can be cut into a short taper, a fade, or an undercut. The classic variation of this cut is neat and slick, but the more modern takes can incorporate texture or emphasize natural waves.

Messy Quiff

The messy quiff is a popular hairstyle for men who want a modern twist on a classic style. As a style that became mainstream after Elvis and James Dean, the quiff is characterized by its sheer volume, which is usually three or more inches high just above the forehead. The messy look applies to the voluminous section of hair, which often boasts a bit of disheveled fringe. The contemporary version of the cut emphasizes the difference in length top and the sides, but the traditional version is much softer and far less severe.

Slick Side Part

The slick side part is a dapper look that was commonly worn in formal settings. This classy hairstyle features a pronounced part with shiny, slick hair that runs almost perfectly perpendicular to the side. While most modern gentlemen prefer a textured look, the 1950s side part can be achieved with an oil-based pomade and a standard comb for that perfect wet finish. While you can choose a taper on the sides and back, a skin fade offers the contrast for a bold touch.

Wavy Swoop Pompadour Fade

The wavy swoop pompadour fade is a modern adaptation of the classic pomp that combines several elements of other 50s styles. It starts with the traditional 50s-style pomp and a sleek taper fade on the sides, but rather than styling the hair straight upward or slightly off to one side, this style has a very defined swoop. Start with slightly damp hair, apply a strong gel that maintains its wet look, and then direct the hair just behind the forehead upward. Then, carefully tuck the ends of this section of hair just behind the volume to create the wave that gives this look its character.

Textured Cowlick

The textured cowlick is a hairstyle that plays on the funny bit of swirled hair that can appear on the back of the head. While the natural cowlick is almost always found at the crown of the head, with this style, it can be placed anywhere – including the front of the hair. A cowlick can be paired with a quiff, a modified ducktail, or even a high pompadour.

Textured Pompadour

The textured pompadour is a variation of the popular pomp that relies on the thickness of the hair, the addition of layers, and perhaps some heat styling to achieve its volume. Made popular by Johnny Cash, this rugged take on the pomp calls for slightly longer tapered hair around the back and sides with a very noticeable “bump” at the front. This cut is best for men who have thicker, coarser hair and a few natural waves.

Short Sides with Textured Top

The short sides with textured top hairstyle is a classic look that was made popular by Frank Sinatra, who wore it for much of his professional career. This is a hairstyle created more by styling than the cut, and it starts with a slightly longer version of a gentleman’s cut. All your hair must be brushed back with the crown brushed slightly upward and back to shape the look.

Classic Ducktail

The classic ducktail is a unique variation of more common slicked-back styles. From the front, the ducktail looks just like any other greaser cut. At the back of the head, the precision of the cut and styling creates the illusion of a part that looks almost exactly like the rear-end of a duck. To recreate the look, you’ll need a talented barber or stylist who can cut the sides of your hair very precisely, and you’ll also need to keep up with your regular trims.

Short Pompadour

The short pompadour is exactly what its name suggests – a traditional pompadour with only a small amount of height. Back in the 1950s, the classic pomp was popular, but it was often viewed as cheeky or edgy for its time. The shorter variation of the cut made it more accessible to men and younger boys. Famous actors like Sean Connery favored the short pompadour since it provided an interesting and versatile but subtler look.

Quiff

When heartthrob James Dean was spotted sporting a messy quiff, it quickly became one of the most coveted styles of the decade. The cut features longer hair on the top and front paired with shorter hair on the back and sides. It’s comparable to a pompadour, but rather than pushing all the hair on top upward and back, only the front section of hair stands tall with a quiff. The style can be messy, sleek, or something in between.

Gentleman’s Side Part

The gentleman’s side part is the ultimate traditional haircut that exudes class, sophistication and respect. The hair on top is just slightly longer than the hair on the sides and back, and the top section of hair is brushed or combed over from a side part. There are countless ways to wear the style, whether you prefer it to look wet and textured or more natural. This is one of the easiest cuts for barbers and stylists, and as long as you keep up with trims, it’s also one of the easiest styles to recreate at home.

Slick Back

The slick back is a retro style that encompasses a stylish almost-gangster look. In a broad sense, the style involves using a styling product to “slick” the hair back and away from the face. One of the most popular options is the slick side part made famous by actor Cary Grant. This look starts with a traditional gentleman’s cut with some extra length and a very pronounced side part. The hair on the sides, back and top is slicked back to create a cool finish.

Crew Cut

The crew cut is a short hairstyle for guys who want a low-maintenance and masculine look. In the 50s, the cut was viewed as wholesome and clean, and because it was easy to style and maintain, it quickly became a favorite among the military. It’s a simple style that consists of hair trimmed very close to the head, and it is slightly longer on the top than it is on the sides and in the back. The traditional form of the cut involved shaving the sides and back or incorporating a skin fade.

Flat Top

The flat top is a stylish and edgy choice for guys that offered a rebellious look. Military men, young college guys and little boys flocked to their barbers for this somewhat spiky yet still gentlemanly cut. While the sides and back of the hair resemble the classic gentleman’s cut, all the action happens at the top. The barber or stylist brushes the hair at the top of the head straight up and uses scissors or trimmers to clip in the illusion of a flat surface. The flat top can be very short like a crew cut, but modern versions have seen the hair reach several inches long.

Butch Cut

Also known as the brush cut, the butch cut is a very short military-inspired style. Similar to a crew cut, the main difference between a butch and crew haircut is the butch comes with short hair all over while the crew often features tapered sides. The hair is the same length on the sides and in the back, and only slightly longer on top. Back then, this look was popular in the military and among athletes. The same holds true for modern times.

Conked Hair

Conked hair was a popular look for black men from the 1920s through the 1950s and beyond. To achieve the style, stylists used lye to relax and straighten the hair, then created this signature 50s hairstyle. The conk was mostly viewed as a formal style since the lye would burn and damage the hair when used repeatedly. Modern relaxers are still potent, but they are far gentler.

Short Afro

The short afro is a versatile and stylish haircut style for black men who want to maintain healthy natural hair with ease. The style gained popularity because it looked handsome and clean without the need for harmful chemicals. This cut is the predecessor to the huge afros that made their way onto the scene in the 1960s and 1970s.

Jelly Roll

The jelly roll is named after the shape that the finished style resembles, creating a dramatic and daring style from the 1950s. The hair on top was grown quite long, then combed upward and in to create a loop or rolling wave that looked just like a jelly roll. In some styles, just one roll was placed on the side of the head opposite the part. In others, two rolls were placed directly on top of the head. The modern version is subtler, but it is still viewed as daring and different.

Modern Brush Back

The modern brush back can be defined as a mix between a traditional pompadour and a slick back style. The cut requires longer hair on the top and along the crown and a mid fade on the sides. The longer sections of hair are brushed back and slightly upward, and while some texture may be incorporated into the style, it generally does not boast the wet look that was so common in the 50s.

Stylish Pomp Fringe with Fade

If you imagine a voluminous pompadour combined with a mohawk, you can almost picture the stylish pomp fringe with fade style. Like the classic pomp, the hair on top is left long and piled high behind the forehead, but it is also lifted and pulled forward to create a mohawk-like fringe. The sides are kept short with a taper fade, and the addition of a line up to clean up the neck and sideburns gives this look even more bad boy personality.

Contemporary Rockabilly Jelly Roll

Like most modern variations, the rockabilly jelly roll is a retro hairstyle that has stood the test of time but boasts a toned-down and subtler look. The shape of the roll is visible, and the short sides of the hair create contrast, but the simple addition of thick curls and fringe helps to balance the look in a more contemporary way.

Thick Flow Back with Ducktail

The thick flow-back with ducktail style combines the unique appearance of the ducktail with the flow or flow-back style that became popular during the Victorian era. It involves growing the hair to between two and three inches long, then styling it so that the hair moves straight back and perpendicular to the face. The goal is to cut and style the hair so that when it is brushed back, it creates the illusion of a duck tail at the very center of the back of the head.

Cool Breaker Style

A cool breaker was a cut that played on the unique waves that women often wore in their hair as far back as the 1920s. It consists of longer hair on top and short hair on the back and sides, about the same as required for a pompadour. Styling involved using combs, heat tools, and various products to create a pompadour-like shape that consists of long, thick waves moving backward from the forehead.

Coiffed Waves with High Skin Fade

Coiffed waves with a high skin fade are a stylish look for guys who want a bad-boy appearance with a retro feel. The cut is shaped like a French crop with long hair on top and a high or mid skin fade on the sides, but rather than brushing very short hair forward toward the forehead, heat tools are used to create carefully-shaped waves that move across the head from left to right.

Trendy Side Swept Hair

Modern side-swept hair looks have been adapted from the classic cuts of the 1950s. Some cuts are slightly long and involve sweeping the hair back and to the side, but others are kept short enough to incorporate some trendy spikes or a disheveled appearance. Many of the most popular cuts incorporate pompadour-like height, skin fade undercuts, and other features designed to create significant contrast.

Thick Cropped Top with Undercut

The cropped top with an undercut is a short haircut that looks like a crew cut but with longer hair. The longer section of hair starts at each corner of the forehead, and the sides are all one length without any kind of taper or fade. This versatile cut can be spiked up, tousled, slicked back or brushed forward.

Popular 1950s Men’s Hairstyles

The most popular 1950s hairstyles for men are the slick back, crew cut, flat top, pompadour, quiff, jelly roll, the conk, breaker and greaser look. These cool and classic haircuts were popularized by celebrities like Elvis Presley, James Dean, Cary Grant, Frank Sinatra, Marlon Brando, Little Richard, Tab Hunter and Nat King Cole. These iconic 50s men’s hairstyles have inspired several modern variations that are still stylish and worth copying. From Ivy League to side part and greaser styles, these trends helped shape American fashion and pop culture.