Why These Ten Classic Hairstyles for Men Are Timeless

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For all that changes in fashion and style, certain things remain constant.

Take pants, for example. Pants will always cover the legs (if only just with loose threads). Throughout the ages there have been short pants, long pants, tight pants, baggy pants, and anything else you can think of. When it comes to classic hairstyles for men, they are like that. The products we use in our hair, the tools we use to style it, and the end result may change. But the fundamental, bare-bones styles that men choose for their hair have remained all-but unchanged.

Sure, some of these classic hairstyles for men may appear dated to you. You may know some of them not by their names but rather as “the George Clooney” or “the Johnny Depp” or “The Kid from Kid ‘N’ Play.” Sometimes these looks are more popular than they are at other times. However, this doesn’t take away from the classic nature of these styles. Show up to work tomorrow with “the James Dean” and all anyone will likely say about it is how great you look. Don’t believe us? Keep reading.


What's the Big Deal with Classic Hairstyles for Men?

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Even without the heavy societal pressure on men’s looks that there is on women, it can be a nerve-wracking thing to take a style risk. Many men and boys don’t really worry about their hair, leaving it short, and often forgetting to comb it. It all seems like so much work and not without a little vanity.

Shove those thoughts from your mind with great prejudice. Yes, men don’t face the same fashion pressures as women, but your appearance definitely matters. Forget that potential employers or partners can have their heads turned by a stylish and fashionable look. Forget that your own personal style is a kind of artistic expression we all participate in. All you need to know that even though messing with brushes and combs and hair products can be a pain, the results are worth it.

With the right hairstyle, you can find your confidence soaring to levels you didn’t know were possible. You can send subtle messages, like that you’re an aggressive businessman or a rock ‘n’ roll bad boy. Most of all, you will feel great and, likely, have fun with your new look.

What Haircut is Right for Me?

This is a question that eludes many men, especially those who’ve never cared much about their hair before. Essentially, you can sport any look if you love it, because your confidence will carry you through. Yet, one thing to consider before selecting your look is the shape of your face. Certain hairstyles look better with certain face shapes, while others don’t look good at all.

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If you have a round face, you’ll want to avoid the middle-part or the buzz cut. If you have an oval or rectangular face, you will want to avoid the quiff or the pompadour because they can make your head look larger than it is. These aren’t hard-and-fast rules, of course. You can pull off whatever style gives you the most confidence. However, if you’re unsure about which style to adopt, consider asking your stylist or barber what works best with the shape of your face. Leave it to the experts, and you can tweak the style from what they decide. 

What About the Texture of My Hair?

The reason there are so many classic hairstyles for men is because men all have different textures of hair. From thin and straight to thick and curly, the texture of your hair will determine what hairstyle you choose more than fashion trends or your own likes.

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People with thin, wispy hair are unlikely to ever be able to sport a hi-top fade. People with tight, unruly curls will likely never master the pompadour. The best thing to do is find a barber or stylist whose skills and opinion you trust. With both hair texture and face shape, they will know what looks you can pull off and which ones you shouldn’t try. They will also know about all the amazing products you can use to cheat your way into a look that your hair couldn’t handle otherwise. Still, just accept that thanks to the genetic lottery there are just some styles that you can’t master. But don’t worry, there are dozens more you can.


Classic Hairstyles for Men That Look Polished and Suave

With a few considerations in mind, you're ready to head to the barber. Peruse these looks to find one you love. You can even show it to your hairdresser to ensure you get the exact style.

1. Classic Hairstyles for Men: The Side Part

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The Side Part is one of the most classic hairstyles for men, encompassing pretty much every look in which the part is on the side of the scalp. For most of history, however, the side-part style featured longer hair on top than on the sides. Usually the hair is slicked down with product, though you can add volume as your confidence allows. If you have thick hair, you will need heavier products to keep the style in place. Consider a cream or a paste over gel or hairspray. The final reason that this is such a classic style for men is because the hair naturally parts on the sides, making this easy to recreate at home.

2. Classic Hairstyles for Men: The Buzz Cut

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From Robert DeNiro’s crazed taxi driver Travis Bickle to every new recruit in the United States Military, the buzz cut is the look. This is a hairstyle most people can maintain on their own, so long as they have a pair of electric clippers. While some examples take the buzz as low as they can, it doesn’t always have to be that low. In fact, in the civilian world, the buzz cut is sometimes known as “the Number Five” because the clipper extension leave’s 5/8ths of an inch of hair on the scalp. This is an easy look to maintain, too. If you end up sleeping on your hair and flattening it out, a simple run under the shower will snap things back to where they were.

3. Classic Hairstyles for Men: The Pompadour

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The pompadour is often thought of as one of the classic hairstyles for men who loved motorcycles or early rock ‘n’ roll in the 1950s. However, this hairstyle originated as one for women, named after King Louis XV’s mistress Madame de Pompadour. Immortalized in history and on Doctor Who, this royal lady is known for wearing her hair swept high and over her forehead. In fashion for women from the 18th century until the mid-20th century, men started wearing the now-iconic version in the 1950s, most famously Elvis Presley and Little Richard. In the late 1990s and early 2000s thanks to shows like The Sopranos and Jersey Shore the style saw a comeback. Today, the hipster crowd might favor them, but for the guy with the hair to pull it off, it’ll always be cool. 

4. Classic Hairstyles for Men: The Hippy-Dippy Freak

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This entry on our list of classic hairstyles for men is a bit of a cheat, because it’s really an invented catch-all term for long, scruffy hair. Whether it’s shoulder-length or just long enough for an Afro, this is the style worn by rebels and people who love using hair products. Men have worn long-hair throughout history. It wasn’t odd to see a man sporting a ponytail in Revolutionary War times just as it wasn’t odd to see one in the mid-1980s. Heck, even the mullet belongs in this category, though it’s hard to imagine a time when it ever looked good. So, if you want to rock dreadlocks, sport long tresses, or surround your head with a halo of hair, this is the look for you. Go crazy with it and have some fun. Just know that the longer your hair grows, the more frequent maintenance it requires. (Yes, even dreadlocks.)

5. Classic Hairstyles for Men: The Messy Quiff

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This cut is the cousin to the pompadour and the style of choice for bad-but-pretty boys. James Dean, young Johnny Depp, and David Beckham all have worn this style, although Dean is the one who made it iconic. In this style, the hair is swept back and up from the face. However, rather than styled up in a sweeping cliff of hair, the quiff sweeps it off to the side slightly. This is also the “root” hairstyle for most of those deliberately messy hairstyles worn by the likes of Robert Pattinson in his glittery vampire years. This is a high-maintenance hairstyle and may be harder to keep than it looks. Still, if you can get this volume, this could be your signature style. 

6. Classic Hairstyles for Men: The Middle Part

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While the side-part is perhaps the most iconic of the classic hairstyles for men, the middle-part belongs on this list, too. Naturally, this style is one which features the eponymous part and works with almost any length of hair. Most famously, people will remember this look from the mid-1990s, when young teen heartthrobs like Jonathan Taylor Thomas, Brad Pitt, and a young Leonardo DiCaprio. Of course, it had its time in fashion during the turn of the 19th and early 20th centuries, too. Even when it was out-of-fashion, you could see this hairstyle in the media of the time on “rural” folks. If you want to rock this look today, the longer you can grow your hair, the better.

7. Classic Hairstyles for Men: The Fade

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Originally known as the “taper cut,” a fade is a hairstyle that is popular with people who have all types of hair. Essentially the hair is cut and styled on top, then the stylist or barber cuts the sides in different lengths. For longer hair, scissors and a comb are used to taper the back and sides. However, most stylists today use clippers, especially if the hair on top is short. A variant on this style is known as the Hi-Top Fade, which became popular in the 1980s and 1990s hip-hop scene. The hair is kept very long on top and the styled straight up, almost resembling a pencil eraser. While dated, some folks still wear the hi-top fade today.

8. Classic Hairstyles for Men: Slicked Back

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In the vast majority of the classic hairstyles for men, the hair is brushed backwards and away from the face. However, the slicked back look is not simply brushing your hair to the back. No, this look is specific. Rocked by the likes of Don Draper, the main character of Mad Men, and Jon Hamm, the real-life actor who played him. It’s a look usually sported by folks in business settings by those who play the game aggressively. The only drawback to this style is your hairline. If you have a prominent widow’s peak you run the risk of looking like Squiggy from Laverne & Shirley. If your hairline is receding, this style will highlight that. Otherwise, this is a good alternative look for folks rocking side-parts, middle-parts, and certain styles of quiff. 

9. Classic Hairstyles for Men: The French Crop

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The French Crop is a style that comes and goes in fashion, but one that will always work should you opt for it. The sides and back are tapered, while some or all of the top is combed forward. In the 1990s, this style was most popular thanks to George Clooney sporting the look at the height of his ER fame and transition to features. Today Thomas Shelby sports a version of the style, with longer bangs than usual, for his stint on the Netflix drama Peaky Blinders. This is a relatively low maintenance hairstyle, but once you commit to it you are stuck with it. So make sure you love how you look, or the buzz cut will be your only alternative. 

10. Classic Hairstyles for Men: Bald, Baby.

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Okay, technically a bald head is not considered a hairstyle, let alone of the classic hairstyles for men. But, there is no denying that for some folks, it makes a statement. If you are losing your hair or simply just like the look, you can make your dome shine. For not having any hair, this look still requires maintenance. You have to shave, with a bladed razor, your pate making sure it is clean of stubble. You also can buy products to make your head shine in a natural way. Still, it’s easy to do at home. Tough, charismatic guys from Telly Savalas to Bruce Willis are known for this look. That’s good company to keep.


How to Make These Hairstyles Look Fresh and Fashionable

With the exception of the final entry, these classic hairstyles for men are not cookie-cutter looks that work in all eras and situations. If you decided to rock an eyebrow-length middle-part to work tomorrow, be prepared to hear lots and lots of “the 1990s called and wants their style back” jokes.

Instead, either go much shorter or much longer with your hair. You might even want to stagger the part a little, giving the style a more casual feel. With any of these basic hairstyles, you will need to do a little tweaking to keep them fresh and current.

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There are two ways you can do this: you can either ask someone for their opinion or go with your gut. You should always talk to your barber or stylist about how you can recreate the hair magic they made at home. Usually, they will add their own little stylistic flourishes that can serve as a benchmark for you. Similarly, you could ask a hip friend or even your kids (if you can trust the little devils to be honest about what’s cool) for suggestions.

But ultimately, you’re going to have to go with your own instincts on this. Remember, your hairstyle is an expression, a statement made without words that can color people’s impression of you. You have to feel good sitting under that mop of hair. So, make sure that whatever you do to your hair, you like how it looks, and how it makes you feel. 


Remember, When it Comes to Hairstyles You’re Not Alone.

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Taking a proactive approach to style or changing your tried-and-true look is a big deal. There is nothing wrong with feeling nervous or intimidated by it. It’s normal, in fact. The great thing about this is that unless you are cutting your own hair, you are not in this alone. As mentioned above a few times, your main partner in this effort will be your barber or your stylist. (And don’t listen to your high school friends or your little brother, real men can see a stylist.) They are working for you and tipping is customary, so they want to make sure that you end up with a look you love.

Ask them questions about different styles, figure out the shape of your face, and ask for coaching about how to recreate the look at home. All of these questions and more are what the barber or stylist is there to answer. Sometimes they can be overconfident or too-assertive when it comes to pitching a certain look. It’s okay to be put out of your comfort zone a little, especially if you are trying to make a bold change. But remember, you have to live with the cut, so if it’s not working -- say something. Any stylist or barber would much rather have a happy customer than an unhappy one who takes their suggestions without any push-back.

Did you enjoy our list of the classic hairstyles for men? Did we leave any off? Let us know what you think in the comments below. Also let us know which look you or the man in your life decided to go with. Remember to share the article on Facebook and Twitter!

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