The first thing that comes to our mind when thinking about 1950’s fashion is the incredible Teddy Bear rock music, leather jackets, and very carefully studied hairstyles and grooming techniques! These hairstyles initially took inspiration from the Edwardian Age and rapidly grew into a whole fashion trend in England and the US. Other fashion icons that set the trend in those days were Marlon Brando, Elvis Presley, and James Dean. Here is our 1950s men’s hairstyles list.
I. 1950 Men’s Hairstyles Inspired by the Teddy Boys
1. Classic Teddy Boy Hairstyle For Ginger Hair
What to ask your barber
Start by cutting the front hair to an approximately 2 inches length and shaping an Elephant’s Trunk from the front strands while cutting it really short at the back and keeping natural sideburns.
2. Teddy Roll Haircut with High Pomp
What to ask your barber
A Teddy Roll or a very well styled Elephant’s Trunk haircut will help you improvise a cool look for your top strands just by using a high resistance hair pomade and a hairbrush to curl the top strands and keep the sides slightly faded.
3. Teddy Boy Hairstyle For Paul McCartney
What to ask your barber
This fringy, messy, short haircut with a cool fringe that covers the forehead halfway through is really a cool example of a laid-back Teddy Boys-inspired haircut.
4.Teddy Boy Style Pompadour
What to ask your barber
With the right outfit comes the right haircut: a very sleek, well-groomed Pompadour haircut with strands no longer than 2 inches and a super well-shaved beard will give you the perfect Edwardian inspired look for an authentic Teddy Boy!
5. Widow’s Peak Pompadour With Side Fade
What to ask your barber
This cool hairstyle has short trimmed strands at the back, similar to a Mullet haircut and it gradually increases towards the top into a very well-groomed Pompadour with faded sides.
6. Long Trimmed Hairstyle with D.A.
What to ask your barber
This is an evergreen hairstyle known as The duck-tail or the duck’s ass (D.A.), a shape apparently invented by Philadelphia barber Joe Cirello in 1940, which combines trimming and combing of the hair so that it has the appearance of a feathered duck’s back.
7. White Colored Sleek Pompadour With Long Trimmed Beard
What to ask your barber
After growing your beard long enough to reach the chest you can opt for a similarly long top with shaved sides and a swirly ice-cone-shaped top with a small slope on a side that you will comb using grease or hair pomade to create a great, well-defined texture.
8. Jelly Roll Rockabilly Hairstyle
What to ask your barber
The Jelly Roll gets its name from the combing technique that resembles the appearance of something like a Swiss roll cake. Both sides are combed into a mirror image of each other. In this case, the long sideburns give that specific 1950s men’s hairstyles accent!
9. White Platinum Blonde Hairstyle With Wavy Top
What to ask your barber
If you want to make your hair the first thing to get noticed when entering a room, this bleached blonde hairstyle with faded sides and a long, swirling top that looks very much like an undone Elephant’s Trunk is the best choice!
10. Curly Pompadour with Jelly Rolls Hairstyle
What to ask your barber
This amazing 1950’s men’s hairstyles Pompadour is cool thanks to the precise length that allows exposing the natural curls with no styling needed.
11. Swoopy Top with Gray Colored Strands Hairstyle
What to ask your barber
Ask for a tapered side with a long, slightly tilted top that you will carefully arrange to resemble an ice-cone-top using a blow-dryer and a comb while the back strands are carefully gathered at the back.
12. The Rockabilly Ted Hairstyle
What to ask your barber
Short, sleek side parts and a long central line that follows the center of the forehead falling into an undone quiff over the face are the minimalistic versions of the Teddy Boys classic haircuts.
13. Shinny Blue Elephant’s Trunk Hairstyle
What to ask your barber
The style the color, the pose, everything about this retro 1950’s men hairstyles look is absolutely amazing and can be worn with or without styling it thanks to the generous overall length of 3 inches.
14. High Swept Pompadour With Falling Strands
What to ask your barber
Ask for an old-school Pompadour with a modern twist in the front that is simply obtained by taking two different strands and letting them fall around the forehead while cutting the sideburns at a cool tilted angle. What a great result!
15. Slick Back Haircut with Bald Patches
What to ask your barber
If you are interested in Silver Grey Hair Ideas, ask for this slick-back haircut that is a popular 1950’s men hairstyle option especially suited for those with bald patches that want a natural, yet groomed look.
16. Taper Hairstyle With Flowy Top 1950’s Hairstyle
What to ask your barber
While the back and the sides are shaved to a 1/4 inches length, the crown area is left long and free-falling around the sides to create a swoopy, smooth top that will make your look less aggressive.
17. Classic Rockabilly Pompadour Hairstyle
What to ask your barber
This contrasting look is a very cool combination of shortly tapered sides and a long, flowy top cut with wavy strands that can amplify your hair’s volume in an impressive way, or as your barber might recognize it: a Psycho Wedge, Pompadour, and Jelly Roll crossover. A rockabilly classic!
18. Two Colored Jelly Rolls Hairstyle
What to ask your barber
One part blonde, one part brunette, and 100% cool looking 1950’s men’s hairstyles exhibit! This impressive look is surely a good revamp with modern influences of a Pompadour with Elephant’s Trunk hairstyle designs.
19. Sleek Pompadour with Faded Sides Hairstyle
What to ask your barber
Ask for a low fade with a gradual increase in length towards the crown that will still allow your haircut to gain weight and natural texture. Leave the top strands shortly cut to increase the volume on one side creating a “swan”-shaped hairstyle with a thin side part.
20. High Fade with Greasy Pomp Hairstyle
What to ask your barber
Ask for a high fade with clean shaped sides and nape and a 3 inches long crown with a slightly longer front than the back and make sure to keep the strands swept on the back to amplify the natural volume.
21. Sleek Gray Hairstyle with Long Mustache
What to ask your barber
This combover is a classic 1950’s men hairstyles option, suited for those with a receding hairline that look for ways on how to increase their look with minimal styling effort. All it takes is a high resistance hair pomade.
22. White Grey Pompadour with Small Beard Hairstyle
What to ask your barber
The amazing shape of this 4 inches long Pompadour makes a cool contrast with the zero faded sides and can be combined with a small, round beard to obtain a balanced 1950s men’s hairstyles.
23. High Pompadour with Falling Strands Haircut
What to ask your barber
A leather jacket and a long trimmed Pompadour with extra-long sideburns are the perfect match for a classic 1950s men’s hairstyles, or for a retro biker-look!
24. Mullet Pompadour Haircut With Dark Violet Strands
What to ask your barber
Although it might be a bit too much for a day-to-day look, this mullet haircut with a Pompadours Top is a cool looking combination that you can style in many other ways as well!
25. Red Colored Pomp With Bright Ginger Strands
What to ask your barber
Ask for a perfectly finished hairstyle with a cool long ginger Pomp that will make your appearance extremely well-groomed and clean looking in a formal suit!
II. Pompadour Style 1950’s Men Haircuts
26. Clipper Over Comb Pompadour with Beard
What to ask your barber
Ask for a natural colored Pompadour with clipper-over comb technique that you will arrange with a light, hair pomade to obtain a flawless look.
27. High Swept Pompadour with Skin Fade
What to ask your barber
The best way to add inches to your height is to opt for this 4 inches long Pompadour with razor-faded sides and super smooth, silky top that will create a cool contrast with a stubby, unkempt beard.
28. Pompadour Mullet Hairstyle with Blonde Tips
What to ask your barber
If you have plenty of hair and look for a unique hairstyle, this impressive Mullet haircut with perfectly combed sideburns and blonde-orange colored tips is a cool Rockn’roll look that suits both the 50’s and the 80’s!
29. Blonde Colored Pompadour with Long Sideburns
What to ask your barber
A cool way to personalize your Pompadour is to opt for a superficial hair bleaching so as to create a blonde top layer and keep the natural dark color underneath.
30. Rockabilly Pompadour 1950s Hairstyle
What to ask your barber
Asking for an overall longer haircut will allow creating curls at the top part of this Rockabilly hairstyle which could easily pass as an Elephant’s Trunk haircut as well.
31. Metallic Green Pompadour with Falling Strands Hairstyle
What to ask your barber
This perfectly shaped hairstyle is styled using a high resistance hair pomade that allows the natural strands to stay stick-straight above the forehead while some fall around the forehead in a carefree manner.
32. Long Trimmed Pompadour 1950’s Men’s Hairstyle
What to ask your barber
This classic Pompadour has a modern accent thanks to the sharp side fade that brings the hairstyle closer to a short haircut, while the top part is made to resemble a 1950’s men hairstyles thanks to the small pomp above the forehead.
33. Angled Pompadour Haircut with Skin Fade
What to ask your barber
This sleek Pompadour haircut could easily pass as Flattop if it weren’t for the angled cut around the sides that make it cool looking and that gains ultra-volume just by blow-drying it.
34. High Taper With Pompadour and Short Beard
What to ask your barber
Ask for a natural look with a high taper of approximately 1/4 inches length and a long trimmed top that you will arrange on the back to get a shiny, slim look and a stubby beard.
35. Two Sided Wavy Pompadour with Silky Top
What to ask your barber
Prepare for long stares and compliments for your hairstyle with this contrasting haircut that has short faded sides and a 4 inches long top with a slightly curvy shape that will make your look unique!
36. Sleek Pompadour with Faded Cut Hairstyles
What to ask your barber
Ask for a subtle, gradual fade around the sides reaching a 1/4 inches length and a 1 inch long top to allow your barber to style it into a minimal Pomp hairstyle.
37. Soft Wavy Pompadour with Red Highlights
What to ask your barber
Add a splash of color to your haircut with this cool hairstyle with faded sides that reveal the silver-gray hair strands and a long top that you can style in many ways.
38. Sleek Side-Swept Taper Haircut with Deep Side Part
What to ask your barber
This finely chiseled haircut has short trimmed strands and a cool deep side part that allows arranging the strands in various ways until reaching a cool, natural shine that will enhance the golden shade of your blonde hair.
39. Flattop Boogie 1950’s Hairstyle
What to ask your barber
Ask for a Flat top hair with a very neat trim and well-combed scissors cut to give the cut its specific shape, a great variation that has also stood the test of time since the 60’s until now.
40. Pompadour Fade Haircut with Side Part Hairstyle
What to ask your barber
This finely trimmed Pompadour haircut has all the chances of stealing everyone’s attention thanks to the short scissors trimmed sides and the sleek, well-defined contours that give it the specific 1950’s men’s hairstyle look.
41. High Fade with Pompadour Hairstyle
What to ask your barber
This is exactly what a 1950’s men’s hairstyle would look like if you would want to adapt it to modern times: simply sweep the top part upwards with a bit of hair gel and you are ready to impress!
42. Long Pompadour with Curly Top Haircut
What to ask your barber
If you have a head full of hair, this impressive mix of Pompadour and an undone Jelly Rolls haircut is the coolest possible way you can manage all that crown weight.
43. Blonde Silky 1950’s Pompadour with Skin Fade
What to ask your barber
Ask your barber to give you the sharpest, smoothest fade and combine it with a 2 inches long top and create a curvy top with a cool high-swept shape.
44. Soft Fluffy Pompadour Haircut
What to ask your barber
Some 1950’s men hairstyles are easy to manage with less product since they can easily be combed into a sleek, natural-looking Pompadour with a fluffy texture.
45. Blonde Colored High Silky Pompadour
What to ask your barber
Although it might not resist high temperatures, this sleek, high swept hairstyle with a 4 inches long front strand can be styled to look glorious and made to resemble a Faux Hawk.
46. Short Pompadour Haircut
What to ask your barber
If you’re looking for a low-maintenance haircut, this short-trimmed Pompadour with faded sides is the best way to increase your hair’s natural volume but needs weekly visits to the barbershop to look this clean.
47. Pompadour Haircut with Bald Patches
What to ask your barber
Again, a perfectly executed Pompadour haircut that requires your barber’s full attention and dedication to create a cool, round shape for your top that will mask the bald patches.
48. Orange Colored Pompadour With Long Trimmed Strands
What to ask your barber
While the strands inside the first superficial layers are bleached and orange-colored those underneath are kept natural to create a cool visual game for your Pompadour haircut.
49. Long Luscious Trimmed Pompadour with Curly Beard
What to ask your barber
The best way to rock straight dark hair is to trim it in a long-trimmed Pompadour with a curly beard that will balance the contrast between the luscious top strands and short wiry facial hair.
50. Wavy Faux Hawk with Elephant’s Trunk Haircut
What to ask your barber
With or without the “Dali-mustache”, this impressive haircut looks like a moving masterpiece that will instantly make your style get noticed.
51. High Fade with Small Pomp Hairstyle
What to ask your barber
This look suits those with an elongated face or a very round one thanks to the short faded parts that gradually increase to a longer top and that create a compact look.
52. Dark Classic Pompadour With Undone Top
What to ask your barber
Some haircuts look better than others if you opt to style them with a light hair pomade such as this short trimmed Pompadour with an undone pomp haircut that has slightly longer strands in the front messily arranged for a carefree look.
53. Classic Executive Haircut with Side Part
What to ask your barber
Part modern, part retro but with a very elegant finish, this 1950’s men hairstyle has zero faded sides that increase the perceived volume of the top hair, making it look spectacular after you comb it and arrange it with a comb.
54. Classic Pompadour Haircut with Beard
What to ask your barber
To ask your barber for a Pompadour, you’ll need a decent amount of hair length to work with. The sides will be undercut, and the hair on top will need at least 4 inches in the front and 3 inches towards the back.
55. Curly Top with Skin Fade Hairstyle
What to ask your barber
If you have naturally wavy hair, this curly haircut is the best you can get close to a Pompadour, thanks to the naturally curly top that allows for a full, voluminous look.
56. Ginger Colored Elephant’s Trunk Hairstyle
What to ask your barber
This luscious ginger-colored hairstyle with perfectly arranged hair strands where both topsides are combed into a mirror image of each other makes for a cool, well-trimmed look that is super original.
57. Classic Pompadour with Skin Fade Haircut
What to ask your barber
Modern times can still have that retro-glam appearance if you opt for skin fade with a Pompadour top where the sides will be faded and the hair on top will reach at least 3 cm in the front and 1 cm towards the back.
58. Classic Side Part With Slick Back Top
What to ask your barber
This look is a typical 1950’s men’s hairstyles look that you can get by tapering the arches and the sides while leaving the strands on top longer to achieve a fringe that you can wear on one side, fixated with a hair pomade or hair spray and adding a side part for your look.
59. Scumbag Boogie 1950’s Hairstyle
What to ask your barber
This look is both elegant and well-groomed thanks to the long trimmed top and has short, tight faded sides that give the cool, rough appearance some men prefer to sport.
III. Classic 1950’s Men’s Hairstyles
60. Skin Fade with Short Taper Haircut
What to ask your barber
This typical college look has short tapered sides with a thin deep side part that will serve as your guard line for how long the crown hair should be. Use a finely toothed comb and hair gel to obtain this sleek look.
61. Taper Haircut with Pomp Hairstyle
What to ask your barber
Unlike other Pompadour haircuts for men, this taper haircut has shortly trimmed strand done with scissors and not electric blades and can be easily arranged with hair gel and a comb to achieve a perfectly defined shape.
62. Psycho Billy Hairstyle With Mohawk
What to ask your barber
Somewhere between a classic Psycho Billy haircut and a Punk Mohawk, this hairstyle is a very well-groomed hairstyle which can make it comparable to the classic 1950’s mens hairstyles.
63. Classic Taper Haircut with Side Part
What to ask your barber
A tapered haircut or a flow haircut will easily be arranged in multiple ways if you opt to add a styling product and comb the hair afterward to gain this impressive shine and definition for your long strands.
64. Sleek Taper Haircut with Side-swept Top
What to ask your barber
Ask for a tapered top and sides with an approximate overall length of 1/2 inches and apply a bit of hair gel on the front strands to curve them over the forehead.
65. High Fade with Slick Back Hairstyle
What to ask your barber
This cool Pompadour has shaved sideburns and a short crown area where the level gradually increases towards a 3 inches top length while the top is slightly longer and has a shiny, well-kept appearance.
66. White Grey Colored Hairstyle with Long Mustache
What to ask your barber
The natural classy Pompadour is here mixed with a German-inspired look with a long mustache and short trimmed beard that will give you a forceful appearance.
67. Slick Back Blonde Pompadour
What to ask your barber
With a cool, natural shaped Pomp and short tapered sides, this short haircut for men with blonde hair will put your beautiful hair on display and go great with a thin mustache and beard.
68. Greasy Slick Back Hairstyle with Receding Hairline
What to ask your barber
No better way of integrating a receding hairline into your cool hairstyle than by cutting the top part to an approximate length of 2 inches and comb it with a hair pomade to obtain a voluminous crown.
69. Slicked Back 1950’s Men’s Hairstyle
What to ask your barber
Get a medium haircut with an even length of 2 inches and add a couple of highlights to obtain a lighter shade and enjoy a cool appearance, worthy of a dandy or a modern Teddy boy!
70. Greasy Executive 1950’s style Haircut
What to ask your barber
The main element of the Executive haircut is always the well-trimmed, sleek top and short tapered sides and the thin side part that you can arrange depending on your hair’s growth direction.
71. Flattop Haircut With Trimmed Sides
What to ask your barber
Ask for a high fade that reaches just above the crown area and a 4 inches long top with a spiky texture that will allow your hair to look fabulous no matter the weather conditions.
72. Ginger Colored Faux Hawk with Side Razor Design
What to ask your barber
This cool ginger shade is beautifully enhanced by the perfectly trimmed curls that are carefully gathered into V-shaped Elephant’s Trunk element which creates a cool contrast with the side razor design.
73. Classic Pompadour Flattop with Faded Sides
What to ask your barber
Ask for a short on the sides long on the top hairstyle with a short transition towards a maximum of 1-inch top that will make you gain extra inches to your height.
74. Blonde Hairstyle with High Mohawk
What to ask your barber
This cool, spiky look has all the retro-elements of 1950’s men’s hairstyles such as a D.A. mixed with an undone Pompadour haircut and the added bright orange shade makes for a cool appearance.
75. Executive Taper Haircut with Side Parted Hairstyle
What to ask your barber
Clean the sides and the nape while keeping the long beard and gradually increase the length towards the top where the haircut should seamlessly blend with the receding hairline.
76. Skin Fade with Greasy Pompadour Hairstyle
What to ask your barber
This amazing look is all about the contrast between the low zero fade with the greased, shiny Pompadour top that makes you look super cool and allows multiple styling options.
77. High Combover with Deep Side Part Hairstyle
What to ask your barber
While the sides are shortly faded, the top is kept reaching a 1/2 inches long allowing you to comb it and style it naturally. You can grow your facial hair instead if you’re looking for a darker look.
78. Elephants Trunk Haircut With Falling Strands
What to ask your barber
Ask for a combination between Elephant’s Trunk and a Jelly Rolls haircut with transitional faded sides and a stripe of hair of around 5 inches length, styled so that it hangs above the nose.
79. Blonde Colored Haircut With Long Beard Hairstyle
What to ask your barber
If you don’t have a full, voluminous crown, opting to grow your facial hair instead will help you balance the two levels of your haircut and you can slick it back to display your facial features.
III. Unusual 1950’s Men’s Hairstyles
80. Slick Back Hairstyle with Bald Patches
What to ask your barber
This ultra-messy, high-swept hairstyle suits those with a receding hairline or a V-shaped hairline that can balance the lack of the front hair and allow you to wear it in a man bun or a top knot during lazy days.
81. Silky Executive Cut with Side Part Hairstyle
What to ask your barber
This short trimmed hairstyle has short faded sides and a longer top part separated through a razor-sharp sideline that creates a cool, square-shaped look for your head with minimal effort.
82. High Fade with Sloppy Mop Top Hairstyle
What to ask your barber
Definitely versatile and easy to wear, this short trimmed hairstyle has a curly, bleached top with an irregular shape and skin faded sides for a contrast that creates a cool look for your face.
83. Elvis Presley Tousled Look With Messy Top
What to ask your barber
The legendary rock icon has lost his 3 inches long sideburns in exchange for a messy, high-swept look with an even length of 1 inch at the top.
84. Greasy Slick Back Haircut
What to ask your barber
Ask your barber for the slickest, shortest hairstyle possible that you can style to perfection with a high resistance hair pomade and dramatic eye makeup.
85. High Fade with Pomp Haircut
What to ask your barber
Start by fading the arches as close to the skin as possible and then change the numbers of the clippers blades to a higher level until you reach a maximum of 2 inches at the highest point.
86. Retro Combover with Hard Part And Skin Fade
What to ask your barber
This look is all about the contrast between the faded sides and the long top. When you comb it, start off with a sharp part on the right side of your head. When you create the wave in the front, keep it close to the head.
87. Combover Cut With Side Part Hairstyle
What to ask your barber
This super stylish look has zero faded arches and a slightly tapered look with a deep side part and a stubby beard to help you achieve a dapper 1950’s men’s hairstyles look.
88. Sleek Blonde Hairstyle With Soft Top
What to ask your barber
More than a Rockabilly, this hairstyle has a classic, very well-groomed appearance with a long, swoopy top and it can advantage men with a mature hairline since the longer top makes for a cool natural volume.
89. Ultra-high Flattop Hairstyle
What to ask your barber
Extremely long top and a short, overall fade will help you gain both texture and extra-inches to your height allowing you to style the Flattop haircut in many ways you could think of.
90. Ultra-high Easy Hairstyle with Long Trimmed Pomp
What to ask your barber
For this haircut to be successful, you will need a significant amount of hair available on your scalp and a scissors trim that will create a compact, slightly coiffed top with wavy, fluid top strands.
91. Spiky Flattop With Skin Fade Hairstyle
What to ask your barber
Although it might not be a classic Rockabilly look, this natural Spiky Flattop haircut looks really tough and impressive if you ask for a small beard to go with it and skin fade the rest of the scalp.
92. High Flattop with Skin Fade
What to ask your barber
This impressive haircut looks very similar to a Psycho Quiff but has a wider Hawk compared to the classic look and the greased strands make it look like a 1950s men’s hairstyles example.
93. Long Flattop Hairstyle with Straight Strands
What to ask your barber
Those with thick hair can ask for a 2 inches long top cut at an even length that will give the appearance of the bristles of a brush to your haircut making it resemble a Flattop.
94. Classy Greasy Hairstyle
What to ask your barber
Ask for a subtle D.A. at the back, mixed with a feathered top and short sideburns, and apply a high resistance hair pomade to hold all the hair strands together.
95. Undone Messy Hairstyle With Long Top
What to ask your barber
This freestyle haircut with undone pomp has a slight undercut haircut that reaches approximately 3 inches and the sides are short trimmed for a cool contrast.
96. High Wavy Undone Pompadour Hairstyle
What to ask your barber
With or without the beard, this look is definitely emblematic for the 1950’s men’s hairstyles thanks to the high, undone pomp that requires minimal styling.
97. Sleek Flat Pompadour With Auburn Hues
What to ask your barber
Those with fine hair can opt for this extremely well-trimmed Pompadour that makes the auburn colors really show up and is paired with a cool mustache and clean shaved beard.
98. Executive Cut with Low Fade
What to ask your barber
This classic Executive haircut has a 1 inch wide low fade with a deep side part and a longer top that you can comb and arrange using a hair pomade.
99. High Pompadour with Deep Side Part
What to ask your barber
It’s all about the finesse and perfectly arranged top strands and the equally beautiful sides that make for a cool Pompadour with a retro accent given by the perfectly arranged deep side part.
100. Silky Flattop Hairstyle For Receding Hairline
What to ask your barber
Ask for a 1/4 inches long fade with a gradual transition to a 1 inch long top that you will arrange using a hair pomade and blow-dryer to obtain the perfect Flattop contour.
101. D.A. Vintage Haircut For Soft Blonde Hair
What to ask your barber
Sculpt carefully the back strand to create the perfectly shaped D.A. with soft, feathered layers combined with a small, 1-inch long Pomp in order to create a beautiful shape.
Conclusion
What is the most interesting and cool thing about being a hairdresser? Of course, the result of the work. Plus, you get to travel in time when recreating a vintage style! These 100+ 1950’s men’s hairstyle options are super cool and will help you learn a lot about your personality and fashion taste.
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