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15 Best Old School Haircuts

Old school haircuts have been making a comeback in recent years. While seemingly old-fashioned and retro, these vintage men’s hairstyles transcend time and look just as stylish and classy now as they did in the 50’s and 60’s. In fact, many of the retro hairstyles like the pompadour, slick back, quiff, and side part are barber shop favorites.

To make these old school hairstyles for men fit the latest hair trends, all guys have to do is ask their barber for an undercut or fade on the sides and back and then style a textured finish on top. This natural look will require a matte product. However, to style the most gangster haircuts, you’ll keep your hair slick and sophisticated using a strong hold, high-shine pomade.

To get the best old-fashioned haircuts, check out the classic cuts and styles below. These traditional men’s haircuts work well with short, medium and long hair, and combine the coolest styles of the past with today’s skilled barbering!

Classic Pompadour Hairstyle

Old School Pompadour

The classic pompadour is one of the most popular men’s haircuts of all time. This old yet iconic hairstyle lives on barbershops today with a fade or undercut on the sides and textured styling on top. If you want the traditional retro version of the style, guys should apply a high hold pomade with shine for a slick, wet finish.

If you’re more interested in the modern pompadour, try a matte hair product for a natural look. Either way, this classy men’s hairstyle is edgy and bold.

Old School Slicked Back Hair

Old School Slicked Back Hair

Old-fashioned slicked back hair is another barbershop favorite. As one of the hottest men’s hairstyles throughout history, guys love it because it’s easy to style and maintain. Just use a strong, shiny hair product and brush your hair straight back.

To try the modern slick back, look at the slick back undercut or fade. The short sides and back will highlight the long hair on top, making for a classy yet sexy haircut women can’t resist.

Retro Quiff Hairstyle

Old School Quiff Hairstyle

The old quiff looks very much like the textured modern quiff. Popularized by James Dean, the quiff hairstyle offers a casual, natural styling with volume and length on top. Although you can use a strong hair product to create a less messy, neater version of the look, we recommend a light to medium hold pomade, wax or cream for maximum movement and flow. The end result is a classic men’s hairstyle that will never go out of style.

Traditional Side Part Haircut

Traditional Side Part Haircut

The side part represents a handsome gentleman’s hairstyle. Generally, men’s parted haircuts were common among the sophisticated elite. Ivy League boys, privileged young men, and professional businessmen could be seen wearing the old school side part along with their suit and shiny shoes.

Styling a side part is super easy – simply find you hair’s natural part, brush one side all the way over and the rest down. Modern side part haircuts sometimes add a thick line shaved into the hair to accentuate the parting.

Old-Fashioned Comb Over Hairstyle

Old-Fashioned Comb Over Hairstyle

The classic comb over is often confused with the side part. Although both hairstyles are known for their smart, dapper look, the comb over hairstyle flows more and doesn’t offer the same structured finish as the part. The vintage comb over haircut requires short tapered sides cut with scissors, and a short to medium length top styled with shiny pomade.

However, the comb over fade is a much cooler modern variation. Guys have the choice of a high, mid, or low fade on the sides, with the option of tapering or fading into the skin. Similarly, you can pick an undercut for a one-length cut. Lastly, the hair on top is often textured for a more natural look. The final look is a trendy style that’s hard to beat in terms of versatility.

Gangster Haircuts

Gangster Haircuts - Short Tapered Sides with Side Swept Hair and Full Beard

Gangsters and Hollywood celebrities were the trendsetters for much of the 20th century. However, old school gangsters and mobsters did try their best to blend in, meaning they preferred professional haircuts that made them look like reputable businessmen. These classic gentleman’s haircuts were clean cut and classy with short sides and short to medium length hair on top. The best gangster haircuts you’ll find are the slick back and side part.

Old School Short Haircuts

Old School Short Haircut - Short Fringe with High Taper Fade

While many old-fashioned styles kept hair on top longer, some stayed short all over. Pictured is an example of a clean short sides and back haircut with a short fringe on top. The textured messy styling looked good under the hats worn back in the day. Speaking of, the fringe and French crop have been trending this year.

Rebellious Rockabilly Jelly Roll

Old Fashioned Jelly Roll

This rebellious Rock and Roll hairstyle was huge in the 40’s and 50’s. Named the Jelly Roll, it was common among guys of the Rockabilly and greaser era.

Retro Finger Waves

Old Fashioned Retro Finger Waves

The finger waves hairstyles were a good look among guys with wavy or curly hair. Much like a side part, the longer hair on top was brushed to one side, where the curls or waves were left tousled. Although handsome for the time, the styling hasn’t appeared much since the 20’s.

Old School Bad Boy Haircut

Old School Bad Boy Haircut - Short Classic Taper with Long Messy Quiff and Stubble Beard

The old school bad boy haircut doesn’t change much from decade to decade. This example shows short sides that are tapered with scissors, medium-length to long hair on top, and a stubble beard. The free-flowing, natural hairstyle offers volume and movement that defies the prevailing gentleman’s style of the day, therefore exuding the bad boy image. The modern version would be today’s hot hipster haircuts paired with a thick beard.

Classic Old Western Cowboy Hairstyle

Classic Old Western Cowboy Hairstyle - Shaved Sides with Thick Slicked Back Hair and Mustache

The short sides, thick brushed back hair, and full handlebar mustache provide the perfect cowboy hairstyle. Because cowboys were known to be alpha males, this old-western hairstyle symbolizes their rebellious and masculine style.