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55 Vintage 1920’s Hairstyles For Men – Classic Looks For Gentlemen

In the 1920’s gentlemen were serious about their appearance and most men still wore hats whenever they were out.

The majority of haircuts during this time were worn flat and slicked back so that if the men took their hats off they would not have messy hair underneath.

There weren’t that many styling products for men in this era either – some even used Vaseline to slick back their locks! 1920’s hairstyles for men are making a big comeback – here are some classic examples:

# 1 Vintage Undercut

In this style, the hair was shaved into a two-step undercut, separated from the longer upper locks by a slightly centered parting.

There is a little lift over the forehead and shortest hair along the side matches the length of the sideburns and beard.


# 2 Old School Is Cool

In this picture, the hair was cut into a high undercut along both sides and the longer hair on top has been slicked back and to the side with a slight rise in front.


# 3 Sleek And Stylish

The top locks were brushed back behind a short center parting to create this stylish look.

To get this look make sure your locks are straight and don’t flatten the hair out. Add a high undercut on the sides.


# 4 A Dash Of Pompadour

While men’s hairstyles of the time were generally a little flatter than this you can add some lift to your 20’s inspired style.

This is a good example to follow – keep it short on the sides and allow a smooth rise above your forehead.


# 5 Pristine Skin Fade

For this clean looking hairstyle the stylist has used a razor along the parting to widen and define it. The sides feature an expert skin fade and the rest of the hair has been combed finely and smoothed out.


# 6 Smooth Wave

Here there is a skin fade along the sides and the upper hair has been sleeked back over a natural looking wave. This provides texture and lift to this vintage look.


# 7 Picture Of Elegance

In this picture, the model has opted for a razor fade on the side that connects into his sideburns and used pomade to achieve that slick comb over.


# 8 Lift And Taper

Here we see a pompadour style with the hair combed over into a rise in front that gently tapers off towards the back.

He’s wearing it with a high parting that runs up to the crown and a curved undercut.


# 9 Match Your Style

If you want to wear a 20’s hairstyle, make sure you match the rest of your attire too! Here we see a classic dapper look with skin fade and pompadour lift combined with braces and a clean shaven face.


# 10 Natural Gentleman

Not all 20’s styles need to be smoothed down – this model is wearing a more relaxed look with a high parting and wavy locks that have been styled with finger combing.


# 11 The Definitive Cut

In this picture, the hair has been expertly snipped to have clean edges and a gentle fade out on the side.

To style the locks have been brushed up and back, creating slight lift in front, and smoothed with pomade.


# 12 Leo’s Luster

In this picture, Leo wears a classic comb-over style with a little wave in front before the hair was smoothed flat to the side.


# 13 Long Trim Pompadour

To achieve this look you would need to let your hair grow out slightly before going to the barber. For this style, all the hair from the left side has been finely combed up and neatly set into a smooth coif.


# 14 Top Notch Trim

Here we see a vintage look with clean cut lines and well-defined styling.

This style is perfect for thinning sides as it provides camouflage with the undercut and the pompadour-inspired lift draws the eye upward.


# 15 Be Different

With so many men sporting short shaved sides you may want something slightly different.

You could try this look with slightly longer locks; it also features a tapered cut on the sides along with a little curl in the front.


# 16 Business Contour

This handsome style has great texture and works well with naturally wavy hair like his. It features a neat parting and skillfully blended sides, together with natural lift and a side comb over.


# 17 Simply 20’s

If you want a simple, no-nonsense look that is easy to style in the mornings try this one. Here we see the upper locks brushed back smoothly and held in place with the product while the sides are graded.


# 18 Luxury Locks

For this look, the sides are slightly shorter than the top locks and are being worn combed down. The upper hair is brushed back with a little curl over the forehead.


# 19 Slicked Back

To get this slick look ask your barber for a pomade product to hold your vintage style in place.

In this picture, all the hair has been combed back, apart from a small section in front that has been styled up into a quiff.


# 20 Texturized Sides

Here we see a graceful undercut on the side, with texture in the upper layers and a high rise in front.

Remember to keep the lines of any pompadour look rounded and smooth if you want to be true to the style.


# 21 Finely Tuned

In this look, the high, defined parting gives the style balance and allows the skin fade to contrast the raised coif on the opposite side.

To achieve this look you’ll need to start with super straight hair and use a fine comb to lift the locks.


# 22 Bald Fade

A bald fade is where the graded undercut ends in a layer of bare skin. In this example, the fade has been used to cover thin hair on the sides and draw attention to the slightly longer, brushed back locks on top.


# 23 Provide Contrast

If you want to draw attention to a statement feature; like this curled mustache, go with a simple hairstyle.

Here we see a razor fade on the side while the upper locks are combed straight back with a slight lift.


# 24 Mature Vintage Style

Steve Buscemi wears a vintage hairstyle here, showing us how flattering these can be for mature gentlemen. The comb over in front works well to flatter thinning areas and the sides are neatly brushed back.


# 25 Golden Age

While most 20’s styles are more suited to straight locks you can wear natural curls as well. Just make sure that you balance curly sections with slicked back portions like this.


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1920’s hairstyles for men were all about looking neat and creating smooth lines. Nowadays men are combining these vintage looks with quiffs and pompadours to add height as hats are not as popular as they were in the 20’s.

These vintage looks suit most men and will ensure that you look like the perfect gentleman at all times.