Men's Hairstyles Today

The Best Haircuts For Men

  • 2021
    • Best Haircuts For Men
    • Popular Haircuts For Men
    • Business Professional Haircuts
    • New Hairstyles For Men
    • Cool Hairstyles
  • Fade
    • Best Fade Haircuts
    • Taper Fade Haircuts
    • Low Fade
    • Mid Fade
    • High Fade
    • Bald Fade
    • Types of Fades
    • Taper vs Fade
    • Low Fade vs High Fade
    • Temp Fade
    • Drop Fade
    • Burst Fade
  • Undercut
    • Undercut Hairstyle
    • Disconnected Undercut
    • Undercut Fade
  • Short Hair
    • Short Haircuts For Men
    • Men’s Short Haircuts
    • Men’s Short Haircuts For Thick Hair
  • Medium Hair
    • Medium Length Hairstyles
  • Long Hair
    • Long Hairstyles
    • Guys with Long Hair
  • Hair Types
    • Thick Hair
    • Wavy Hair
    • Curly Hair
    • Thin Hair
    • Black Hair
  • Beards
    • Different Types of Beards
    • Best Beard Styles
    • Best Beard Lengths
    • Beard Trimmers
    • Beard Straighteners
    • Beard Shampoos and Conditioners
    • Beard Products For Black Men
  • Boys
    • Teen Boy Haircuts
    • Cool Boys Haircuts
    • Boys Fade Haircuts
    • Long Haircuts For Boys
    • How To Cut Boys Hair
  • Celebrities
  • Reviews
    • Barbers

15 Best Old School Haircuts

Updated February 22, 2021 by Barber James

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!

Contents

  • 1 Classic Pompadour Hairstyle
  • 2 Old School Slicked Back Hair
  • 3 Retro Quiff Hairstyle
  • 4 Traditional Side Part Haircut
  • 5 Old-Fashioned Comb Over Hairstyle
  • 6 Gangster Haircuts
  • 7 Old School Short Haircuts
  • 8 Rebellious Rockabilly Jelly Roll
  • 9 Retro Finger Waves
  • 10 Old School Bad Boy Haircut
  • 11 Classic Old Western Cowboy Hairstyle

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.

3K Shares
Share
Pin
Layrite Pomade

Layrite Pomade Review – Deluxe Original and Super Hold

Layrite Super Hold and Deluxe Original Pomades are some of the best water-based pomades you’ll find. ...

[View More]

Hair Products For Long Hair

10 Best Men’s Hair Products For Long Hair

Looking to get the best hair products for men with long hair? We reviewed the leading men's grooming ...

[View More]

Suavecito Pomade Review

Suavecito Pomade Review

Suavecito Pomade may be the most popular hair product and best pomade for men. In fact, Suavecito ...

[View More]

Best Hair Loss Shampoos

7 Best Hair Loss & Growth Shampoos For Men

If you are balding or see thinning hair, then finding the best hair loss shampoo is important for ...

[View More]

The Best Dandruff Shampoos For Men

Best Dandruff Shampoos For Men

If you're searching for a dandruff shampoo that will get rid of an itchy dry scalp, then you'll ...

[View More]

Best Cheap Beard Oils

5 Best Cheap Beard Oils

If proper beard care is important to you, then you're probably buying beard oil. But what if I told ...

[View More]

Best Pubic Hair Trimmer For Men and Women

Best Pubic Hair Trimmers For Men

We tested the best pubic hair trimmers from the leading brands, and the results were incredible. If ...

[View More]

The Best Electric Shaver For Black Men

Best Electric Shavers For Black Men

Shaving as a black man can be challenging and the right razor can make all the difference. The best ...

[View More]

Follow Us!

Follow Us on FacebookFollow Us on PinterestFollow Us on Twitter

New Haircuts For Men

Men's Box Braids with Fade

Box Braids For Men

Taper Fade Haircuts

35 Best Taper Fade Haircuts For Men

Best Haircuts For Boys

50 Best Boys Haircuts

Textured Thick Spiky Hair + Mid Fade

125 Best Haircuts For Men

Professional Haircuts

Professional Hairstyles For Men

Top Fade Clippers

7 Best Hair Clippers For Fades

Cool Teen Boy Haircuts

101 Best Hairstyles For Teenage Boys

59 Best Medium Length Hairstyles For Men

Bald Fade Haircut

Skin Fade Haircut / Bald Fade Haircut

High Fade Pompadour + Beard

Best Men’s Fade Haircuts

Search For Hairstyles

Cool Fade Haircuts

  • Men’s Fade Haircuts
  • Taper Fade Haircuts
  • Skin & Bald Fade Haircuts
  • Low Fade Haircuts
  • High Fade Haircuts
  • Mid Fade Haircuts
  • Types of Fades
  • Low Fade vs High Fade
  • Fade Haircuts For Black Men
  • Best Fade Haircut Styles
  • Undercut Fade

Best Hair Products For Men

  • Best Pomades
  • Best Hair Wax
  • Best Hair Gel
  • Best Hair Clay
  • Best Hair Creams
  • Best Hair Products
  • Pomade For Thick Hair
  • Pomade For Curly Hair
  • Hair Products For Thin Hair
  • Hair Products For Curly Hair
  • Hair Products For Long Hair
  • Pomade vs Gel vs Wax
  • Men’s Hair Products For Every Type
  • Pomade For Asian Hair

Popular Men’s Hairstyles

  • 35 New Hairstyles For Men
  • 35 Cool Hairstyles For Men
  • 50 Best Boys Haircuts
  • 101 Best Hairstyles For Men and Boys
  • 35 Short Sides Long Top Haircuts
  • 27 Undercut Hairstyles For Men
  • 45 Best Short Haircuts For Men
  • Wavy Hairstyles For Men
  • 61 Best Beard Styles For Men
  • 51 Best Hairstyles For Black Men
  • 23 Popular Asian Men Hairstyles
  • Haircut Numbers – Hair Clipper Sizes
  • Haircut Names For Men
  • 27 Military Haircuts For Men
  • 25 Best Hairstyles For Older Men
  • How To Ask For A Haircut
  • What Haircut Should I Get?

Copyright © 2021 MensHairstylesToday.com | About Us | Contact Us | Privacy Policy | Affiliate Disclosure | Do Not Sell My Information | GDPR