5 Classic Hairstyles + Men’s Haircut Tips

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Avoid Hair-Raising Experiences with a Classic Haircut!

Hair is an extension of every man’s style, personality, and grooming aesthetic, so your hairstyle should never be an afterthought. But nowadays, there is a greater variety of cuts for men’s hairstyles than ever before, so which cuts really stand the test of time?

Dozens of men’s haircuts are now popular, from classically inspired styles to those with a considerably more modern flair and from long haircuts to short haircuts. This guide, however, will focus on timeless and versatile styles that offer the best haircuts typical of young adults and mature men interested in Classic Style.

Suffice it to say, trendy hairstyles like the fohawk, excessively long bangs, or man bun will not be discussed here!

Instead, this guide will introduce you to the best men’s haircuts of the classic style that have literally withstood the test of time and will look good on you whether you’re delivering a speech in the boardroom or enjoying drinks in a happening nightclub.

Defining a Classic Men’s Haircut

There are as many types of haircuts as there are types of men, but if you are interested in a Classic Haircut, your hairstyle will need to meet specific criteria that help ensure it is timeless and classic.

A classic haircut:

  • Will look good on most face shapes
  • Can be modified to fit individual needs
  • Falls in the middle in terms of hair length, being neither too long nor too short

Learn our 11 hair hacks for men!

A vintage fashion illustration depicting a cocktail party
A Classic haircut is just about as classic as a classic martini!

These criteria are not necessarily totally objective, so what constitutes a Classic haircut can vary based on your culture, location, and local customs. In general, however, a Classic Haircut will avoid any trendy or ostentatious components that keep all eyes on the hair itself. A classic hairstyle draws the right kind of attention and keeps most of the attention on you and not your lovely locks.

Classic Men’s Haircuts FAQ

What haircut looks best on a man?

Ultimately, the best possible haircut for you must take into account your hair texture and face shape. In general, however, the most appealing and popular haircuts will be neither too short nor too long, offer a balance between the tops, sides, and back, and not be overly distracting.

How to determine what is the right haircut?

Haircuts will look best when they complement your face shape and hair type. A trusted barber will be able to help you determine what haircut looks best on you and will work best with your lifestyle.

How should men cut their hair?

In general, it will be very difficult for most men to cut their own hair. Therefore, you should seek out someone else to cut your hair for you. Haircuts can be done at home or by professionals that work in barbershops or salons. Contrary to what some people assume, yes, it is perfectly acceptable for a gentleman to get his hair cut at a salon.

What haircuts are most popular or trendy right now?

As with most things, you should never allow trends or fads to dictate what you do, and that is especially true with haircuts. Popular men’s haircuts often require extensive maintenance and rely on outlandish styling details to attract attention. Classic and timeless haircuts, on the other hand, will flatter your appearance while keeping everyone’s attention on you and not just on your hair.

What is the proper length for men’s hair?

While how you choose to style your hair is entirely a personal choice, short to medium-length hair remains the most typical length for Classic hairstyles. This is because hair of this length is easy to maintain, is not distracting, and flatters most face shapes and hair types, making it an extremely versatile style for most men.

How often should a man get a haircut?

The time between trips to your barber varies based on many factors: the ideal length for your haircut, how quickly your hair grows, and your personal preference. In general, most men should get a haircut every three to five weeks, but your particular needs could vary greatly.

How should I take care of my hair?

Haircare is an essential component of a gentleman’s regular grooming routine. You should use a high-quality shampoo and conditioner as needed and ensure that any other products you use in your hair will not damage your hair and are generally safe to use.

How often should I wash my hair?

You should run water through your hair every time you bathe. You only need to use shampoo, however, every three to five days, depending on your personal body chemistry and regular activities like exercising or engaging in other activities that make you dirty.

Quick Guide to Haircuts

Use the quick-reference information in this table to help narrow down which of the five following haircuts will most naturally suit your hair texture, needs, and personal style.

NameBest Hair TypeFormalityMaintenance Level
The Prohibition High-and-TightStraight and not overly curly fine to thick hairIntermediate to Formal High Maintenace
The Pompadour (The James Dean)Longer straight or wavy, fine to thick hairIntermediateHigh Maintenance
The Flair Longer straight or wavy, fine to thick hairCasual to IntermediateMedium Maintenance
The Gent Gazette All hair types except for the extremely wavy or heavily textured Intermediate to FormalLow Maintenance
The BedheadAll hair types except very thin or light hair CasualLow Maintenance

The Prohibition High-and-Tight

A Historical Haircut That Still Looks Great Today

This variation on the high-and-tight haircut was very popular, as the name suggests, during the early 20th century. It has enjoyed a revival in recent years thanks to television serials like Boardwalk Empire and Peaky Blinders; many characters on both shows sport similar haircuts.

Like the more traditional high-and-tight crew cut or buzz cut, this variation is typified by the extremely short, close-cropped hair on the sides with a high fade. Unlike the traditional cut, however, the Prohibition High-and-Tight is considerably longer on top.

Variations in Length

The length on top can be altered to fit your personal style. The most classic length will be about two inches, but it can be as long as five to six inches for a more casual, youthful look.

When the hair on top in this style is cut short, the haircut is known as a French Crop.

This haircut looks great because the contrast between the long hair on top and the short sides gives it that rough edge that’s very wild and masculine but not over the top.

A picture of Jimmy Darmody in Boardwalk Empire
Jimmy Darmody sports a longer Prohibition High-and-Tight in Boardwalk Empire [Image Credit: HBO]

Best Hair Textures

For hair texture, this style will work for anything from fine to thick hair as long as it’s reasonably straight and not too curly hair.

Products

Raphael has relatively wavy hair and he can still pull off this style when he uses a very strong gel to make the hair appear more straight. Depending on your hair type, you could also use a pomade, wax, or fiber to a similar effect.

Be aware that as your hair grows out on both the sides and top, this haircut can quickly begin to look very unkempt very quickly. Therefore, you should be prepared to make regular trips to your barber to keep it at a manageable and attractive length.

Learn about our favorite products!

The Pompadour (The James Dean)

The Preferred Haircut of the King of Cool

A photograph of James Dean with his signature hairstyle.
James Dean’s signature hairstyle.

This hairstyle was extremely popular during the middle of the 20th century with teenaged heart-throbs and is therefore often referred to as the James Dean, the American actor who helped make it famous.

Best Hair Textures

To really pull off the James Dean, you will need a relatively thick, textured head of hair on top, but this look can work with straight hair that is fine to thick. To achieve the full James Dean Look, however, you will need to add curls at your forelock to be completely accurate and match the inspiration for the look.

Variations in Length

Nathan gets his hair cut
A barber can help you determine how to make different haircuts work for you.

If you are making the switch to a pompadour, we strongly encourage you first to visit your barber to see precisely how to style your individual hair and make its length work for the cut. But first, you will need to grow out your hair on the top and the sides because this particular style makes extensive use of combing the back and to the sides. If your hair is shorter, you may end up looking more like a porcupine than a rebel without a cause.

Products

Your barber will show you how to style your hair, but bear in mind that this look requires significant upkeep. You will need to employ a variety of products, especially a medium-hold pomade or grooming cream, and make extensive use of a blow dryer. If you do not own a blow dryer, prepare to invest in one if you want to maintain this look.

Royal Crown Pomade

Product Intro

Pomade

Pomade is a classic men’s hair product that is intended to tightly hold hair in place while imparting shine and a delightful fragrance. While not as popular today as it once was, pomade is commonly used in the Classic Style community because it is dependable and easy to use. Be ware, however, because you have an adverse reaction to it, as Raphael does.

The Flair

Get Vintage Flair with the Flair

A photograph of a man with a flair haircut
The Square Cut Flair is the most modern iteration of this hairstyle.

The Flair is a top-heavy haircut that resembles the Pompadour but is less dramatic. It features short to medium-short hair on the sides, often in a taper fade, and medium to long hair on the top that is styled in waves to the right or the left. This styling gives the look a distinct, rakish charm that inspired its name because, when worn correctly, this haircut imparts plenty of flair.

Variations in Length

Although now closely associated with the dramatic coif sported by Michael Douglas as Gordon Gekko in the 1987 film Wall Street, the Flair can be worn with various hair lengths, and in general, a more moderate mop will generally appear more classic. That being said, longer hair that is combed backward can still appear extremely elegant when executed properly.

The most classic variation on the Flair will consist of a square cut, in which the sides of the hair are neatly trimmed and the top of the hair styled in a somewhat tousled wave that is styled straight back or slightly to the right or left. The key is to maintain a certain height and sense of volume.

Best Hair Textures

As with the pompadour, those new to the Flair can seek guidance from their barber on how best to style this look to work with their hair type and face shape, but this look will generally work with any hair that is not excessively textured or curly.

Products

For most men, a mousse will be the best product to ensure adequate hold without appearing sticky, overly shiny, or flat. The product should be lightly worked into the hair, and then the hair combed back with a slight curve to one or other side. Use short, slightly elevated strokes to help give the hair volume.

A woman with a quiff haircut

Pompadour + Flair =

The Quiff

Popularized by the Teddy Boy movement of the 1950s, the Quiff is a unique haircut that combines the height of the pompadour with the density of a flair and has the dramatic effect of a flattop or mohawk. The Quiff can be styled to be more or less dramatic as desired, but in general, this haircut is just a little too outlandish to be considered a truly Classic haircut, despite its pedigree.

The Gent Gazette

Raphael’s Favorited Haircut

Raphael in black tie with champagne
Raphael’s haircut makes him the toast of the town!

This variation combines the best aspects of the masculine Disconnected Undercut and the timeless Side Part, two very popular men’s haircuts, mingling the pleasing hair-length contrast of the former with the neat silhouette of the latter. It is Raphael’s preferred haircut because it is easy to maintain, can be styled up or down, and looks classically elegant while also being unique and memorable.

Variations in Length

The Gent Gazette consists of short-cut hair on the sides with medium to long growth on top, as is typical with a Disconnected Undercut, but parted and neatly arranged, like the Side Part. How the hair is parted plays a major role in the appearance of this style.

Raphael's hairline - then and now
How long Raphael wears and parts his hair has changed as his hairline has changed.

As Raphael has evolved his personal styling, the part has shifted from being in the front, in the middle, and all the way out to the side. Raphael has found the cut appears most clean when the sides are cut short all the way up to create a nice transition. Unlike some of the other more complicated haircuts in this guide, you will likely not need the aid of a barber to figure out how to adapt the Gent Gazette to your face shape.

Best Hair Textures

Raphael's natural wavy hair sans any product.
Believe it or not, this is what Raphael’s hair looks like without any product.

The Gent Gazette can work with all hair types except for the extremely wavy or heavily textured.

This haircut is ideal for Raphael and likely for many gentlemen because as it grows out, the hair can still be styled in such a way as to look neat and well-kempt. Raphael can usually go for three to four weeks before needing a haircut.

Products

The products required for the Gent Gazette will vary greatly depending on the texture of your hair. If you have very fine or light hair, products will minimal hold will be sufficient. If your hair is more like Raphael’s, however, and is thick with considerable texture, a strong product, like the heavy-hold got2b Henkel gel that Raphael uses, may be necessary.

Follow Along as Raphael Styles His Hair

The Bedhead

Roll Out of Bed and Style Your Bedhead

A photo of a man with a bedhead haircut
The Bedhead

“Bedhead” may be synonymous with the messy look of your hair after you have rolled out of bed, but the haircut that bears the same name is a winsome and playful look that can be rightfully considered a “gentleman’s bedhead.” With clear influences from rock-and-roll and even hipster culture, it’s a fun and casual look that might be perfect for you if you prefer hair that is not very formal or serious.

Variations in Length

In many ways, the Bedhead takes its cutting cues from the pompadour. It has shorter sides, often with no or a low fade, with considerable bulk on top, but unlike more styled variations, the hair on top is intentionally left disheveled, allowing for a unique, relaxed appearance with a good blend of fun and refinement. This somewhat messy hair looks especially fetching with a beard.

When cutting, have your barber keep the hair tight on the sides and long on top, but instead of combing the hair back, it should be pulled forward. Tousle the hair gently with your hands to ensure it appears organic and natural and not uniform and boring. If desired, the hair can also fall slightly forward over your forehead and temples, creating a fringe or bands. If the hair is too regular in being brought forward, however, it can resemble a long caesar cut.

Looking for haircuts for men with thinning hair?

Best Hair Textures

The Bedhead can work with nearly any hair texture, depending on how you prefer to still it. Note, however, that very fine or thinning hair may not appear substantial enough to pull off this look and will instead make the hair appear more sparse than it really is.

Products

Depending on the texture of your hair, you will likely be able to wear the Bedhead with minimal product. Potentially, all you will need to do is dampen the hair, dry it with a blow-dryer, and then shape it as desired. Use a matte product with a light hold, like a grooming cream or hairspray. Avoid products like pomades or heavy gels that make your hair appear shiny or stiff. That look will not work with the casual nature of the Bedhead.

A photo of a hair dryer

Product Intro

The Hair Dryer

Believe it or not, a hair dryer does considerably more than just dry your hair. Based on various factors like the temperature, air speed, and how you tease your hair while drying, you can actually use a hair dryer to impart a considerable amount of volume, shape, and texture into your hair. For many classic hairstyles, you will certainly benefit from knowing how best to utilize this unique tool. Consult your barber for more information on how a blower dryer could help style your hair cut.

What Does Your Barber Wish You Knew? Find Out Here!

Classic Men’s Hairstyle Tips

Obviously, there are so many haircuts for men today that it would be impossible to provide a list that covers them all, especially when dealing with drastically different stylings like braids, dreadlocks, or even a ponytail, bowl cut, or flat top haircut. Instead, we have created this list of men’s hairstyling tips that will help you perfectly style your haircut after you have found one that works for you.

Our Top 9 Tips

1
Confident barbers will recommend you to someone in their shop who they think will give you a quality haircut.

Work With The Hair You Have

Always select a haircut that works with your hair type and face shape, never against it. A good stylist or barber will be able to give you any cut you want and will make you feel great leaving the salon, but once you’re home, it’s up to you to maintain it. By choosing a cut that doesn’t suit your hair type, length, or face shape, you’re setting yourself up to fail and, in the process, look ridiculous.

2
Sven Raphael Schneider's unstyled hair

Long Hair Doesn't Necessarily Look Fuller

As men start to lose their hair, they sometimes assume that growing hair longer will make their hair appear fuller. This approach, however, usually backfires and can make your haircut look like some variation of the unappealing comb-over. Ironically, cutting thinning hair shorter actually makes it look thicker because the hairs, which are not as weighed down, stand up with greater volume and therefore appear fuller.

3
Investing in a properly sized pair will far better serve you in the long run.

Shorter Sides Appear Longer on Top

In most cases, people will look at your haircut as a whole. Therefore, if you keep your sides shorter, you can also keep the top shorter, and it will appear harmonious and balanced. Not only if this look easier to maintain, but it can also partially mask early signs of a receding hairline.

4
Oneblade Single edge razor

Shave Your Part

A shaved part looks extremely neat and clean and makes the entire haircut look more formal because the part in the hair can line up perfectly. If you have trouble maintaining a neat part by combing along your desired line, shaving in the part with a razor can be a good solution, just be careful and ensure that you make a clean shave.

5
Shaving Products Group

Invest in Quality Products

Specially formulated products that do their jobs well and work with particular hair types are not cheap. Investing in products that work well for you, however, will pay great dividends by improving your look, style, and confidence.

6
Examples of 2-in-1 combination shampoo and conditioner (which is bad for your hair!)

Don't Shampoo Your Hair Daily

While you ought to wash daily, you do not need to shampoo and condition your hair every time you shower. Doing so can remove healthy and important oils that prevent your hair from drying out. You should, therefore, run water through your hair daily to remove dirt and grime and only shampoo every two to four days. If you have sweated excessively, you can also cleanse your hair with conditioner instead of shampoo, which cleans the hair without stripping oils.

7
Grooming products would make a great gift to someone who truly enjoys skincare.

Have as Many Products as You Need

Do not feel embarrassed or unmanly because you own a large variety of haircare products. These products help contribute to your overall look and should be matched to your particular hair chemistry and the styles you enjoy. Do not be afraid to try out different products until you find something that works for you because just like everyone is different, everyone’s hair is also different.

8
The folding pocket comb was a favorite in the 1930s.

Use the Correct Comb

Combing your hair not only helps to style it, but it also adds volume and keeps your hair and scalp looking as healthy as possible. Cheap combs made of plastic break often, can catch on your hair, and often leave follicles looking wiry or frazzled. Instead, buy a quality comb that does its job right and keeps your hair looking its best. Quality combs are usually made from rubber, horn, or bone, and start at about $20.

9
When enjoying a conversation with your barber, there's no need to turn your head so much.

Befriend Your Barber

In your haircare journey, few things are more important than your barber, who can give you excellent advice and keep your haircut looking its very best. Be respectful and courteous of your barber and his time, listen attentively to his advice, and do not forget to tip: 15% to 20% is typical in North America.

Keep your hair healthy with these tips!

Conclusion

Be sensitive when taking calls during a haircut so you don't waste your barber's time.
No need to phone it in, your Classic Haircut will look great!

Now that you know five of the most classic men’s haircuts, you are ready to find a haircut that works for you. You also have the information that you need to care for it and keep it looking it’s very best. While many trendy hairstyles may be “hair today, gone tomorrow,” the styles and tips we have offered up in this guide will ensure that your haircut is timeless, versatile, and effortlessly classic.

Let us know in the comments below how you like to do your hair and if you have further tips.

Outfit Rundown

Raphael in a casual look consisting a polo shirt, shorts, and sneakers.
Raphael in a casual look consisting a polo shirt, shorts, and sneakers.

Today Raphael is wearing a quite casual combination. He opted for a very casual summery outfit based around a polo shirt. However, he was careful to avoid the flimsy collars seen on many polo shirts and exchanged them for a shirt-style collar with an interlining. It is cleaner and neater, yet you still have the breathable, flexible polo shirt knit. Rather than with a solid color, he went with a mottled yarn with blue tones and white tones, so it’s very fresh but you won’t see stains as easily, and it’s a little different and not so boring.

For his shorts, he opted for navy with white polka dots made out of linen. It’s a very wonderful material for the warmer days because it wrinkles in a very sophisticated way, and it’s different than all the cotton shorts out there.

For his shoes, Raphael opted for the white of the polka dots and went with a canvas shoe that he often wears barefoot. It’s very breathable. Because Raphael doesn’t not sweat very much, it’s fine for summer and a casual outfit like this.

Reader Comments

  1. I live in a fairly major metropolitan area, and my hair has always been best suited to a fantastic clipper cut with short sideburns, high-and-tight. Looks good, exactly as ordered every time I walk in – and nap through the whole process. (Yes, she is THAT good.)

    Just like any service, when you find ‘The One’ – hold on for dear life! It took me over a year to find my barber when I moved here – bouncing from the ‘You have to go to…” salon to the “must have” barber shop . Due to my career I do move, at times, often – and more than I want to. Hazards of the job. But, I never lose contact with my barbers in other cities. Charlotte, NC – Boston (Cambridge!), MA – Fresno, CA – San Francisco, CA – Las Vegas, NV – Denver, CO – Vail, CO… Yes, that often. Christmas cards, birthday and anniversary – ANY occasion to remind them how important they are to making the look exactly as needed, conservative private service butler by day, cowboy on the ranch at night and weekends.

    1. CB — I’m headed out to San Fran/Oakland for a new job and in need of a quality spot; I get my hair cut often w/ low fade military cut (every week…) — would you mind passing along a good barber or two out that way?

  2. Great tips and ditto on the hair products. Skimping and buying cheap never pays off in the long run.

  3. If you are in your mid 50’s to mid 60’s, very short is a good style. I find this works for me with a little gel on the front that tends to make your style look like a crewcut. It actually knocks years off your face.

  4. Great informative article.For the slicked pompadour, how short should the sides be?

  5. Thank you for this interesting article. Do you have specific suggestions for people with very curly to frizzy hairs?

  6. A good, affordable brush is the Acca Kappa military style boar bristle brush. Horn combs actually are better for your hair than plastic ones because the horn brushes have rounded combs, whereas, the plastic ones have sharp edges from where they were molded. For this same reason boar bristle brushes are better than plastic, etc ones. A good hair product that does not leave residue in your hair is Groom N Clean by Suave. It can be found in the drugstore by the Vitalis.

    1. Blake,
      Nobody should use plastic combs. Horn combs are too stiff, and often sharp. Are you sure you don’t mean acetate? The pros use hardrubber, and in my experience it’s the best. Thanks for sharing the product recommendation!

      1. I will have to try a rubber comb then. Do look into the Acca Kappa brush as well. The bristles seems to align each individual hair giving sheen as well as a uniform look that I haven’t found with other types of brushes.

  7. I have to recommend Murray’s Super Light Pomade for many of the classic styles. I’ve tried everything and this is the best as it holds great and WASHES OUT.

      1. I’m an avid Brylcreem user along with a small amount of Layrite Hi-Sheen Pomade, water soluble so washes out nicely.

  8. There is no better bargain than the Ace comb. It is rubber which makes it more comfortable at a reasonable price.

  9. Hi Sven,

    I am sorry that I could not take advantage of your offer, regarding the survey – very busy at work. But thank you very much. I do use Brylcream on occasion, but prefer a “side cut”, very similar to what JFK had during his presidency. Have a great weekend.

  10. Living in Germany, I am surrounded by baldheads and men with time-saving short haircuts. I have very thin hair, but a lot of it. So I decided to let it grow (aged 38 in 2013, having finished with army reserve), have a permanent wave, and combined it with the suitable beard to d’Artagnan style. It is very important to take your time to care for long hair. I use Revlon Equave conditioner, a “Tangle Teezer” and patience to comb my hair. If I haven’t the time to let it dry, I use a low temperature hairdryer. I’ll never understand men in expensive suits having a 10-Euro-haircut.

  11. Good old military high and tight. The less time in front of a mirror the better.

  12. Thousands of years ago when I was near-penniless, a friend taught me to cut my hair with a grooming razor. Yes, it was trial and error but fortunately my hair grew thick and fast, and over time I learned to cut it without mishaps. I still razor cut it today – mainly because I can get a trim day or night when I want or need to. I also use a professional electric trimmer, but not the inexpensive drugstore variety. My mother gave me an excellent boar bristle hairbrush when I graduated from high school, and it is still in service today. I trim the sides a bit shorter than the top and use a part – this style is not dramatic but is low maintenance and goes anywhere and everywhere.
    Another interesting article, Sven!

  13. I’m very fortunate. 56, haven’t lost a strand, naturally wavy, maybe 3 to 4 gray hairs and don’t even own a comb or a brush. I can do anything from the Flair to High and Tight. I even let it grow near shoulder length a few months back. Once the summer humidity hit it had to go. A dime size of Boardwalk Pomade Strong-Hold, shape and go. If it takes over 5 minutes to fix your hair your either hiding something or your being a priss!

  14. The hairstyle that works and looks best for a Man depends on the Man’s lifestyle and Face and Head shape. It’s best to discuss the options with an experienced and seasoned Hairstylist to get the best advice! Happy Hunting!

  15. I appreciated some of the tips you gave for keeping hair healthy. I want my hair to be healthier, so I’ll definitely utilize some of your tips. My favorite one was your suggestion to wash my hair every other day to keep the natural oils in my hair. I’ll definitely try this out.

  16. I appreciate it when you said that a man should try different hair products so that they will be able to point out which one will work best with them. My husband intends to replace the hair care product that he uses after he gets his haircut, so I will suggest this to him. Though, of course, he needs to focus on getting the right haircut first. Thanks for sharing.

  17. My best friend is going to be getting married in a few weeks and he’s asked me to be in his wedding party. I’d love to get a new haircut and style for the occasion. Your point about how if you keep your sides shorter, you can keep the top shorter for easy maintenance and it will be easier to maintain. Finding a good barbershop will be important to get a professional looking cut.

  18. I love that you mentioned getting a good relationship with your barber. Making sure that you and your barber are on the same page is a great idea. My uncle would love knowing this as he looks into getting a barber.

  19. My husband is asking me for ideas on what kind of haircut he should get for the wedding we’ll attend. Thanks for the idea that I can suggest to him to get a James Dean hairstyle so he can get a classic look that he’s always going for. I think he should go to the barber so he can get a great men’s cut that he wants.

  20. I’d also recommend to invest in a good quality horsehair or boars’ hair brush to brush the oils through your hair between washes. Natural hairs don’t build up static electricity and offer a good brush in combination with the aforementioned comb.

  21. Raphael is the last person from whom I would take any advice concerning hairstyles. Has he ever looked at his own head from an even slightly critical point of view?

Comments are closed.