7 Classy Hairstyles for Guys with Medium Length Hair

These classy hairstyles have been proven and tested throughout time. Here are some examples:

There are so many classy hairstyles that you can wear with medium length hair. Because your hair is a little longer, you can experiment with more styles than guys with short hair can. Check out these classy hairstyles that are guaranteed to give you and your hair a fresh new look.

Classy Hairstyles for Medium Length Hair # 1


The great thing about having medium length hair is that you have more hair to work with. Medium length hair also provides you with the flexibility to enjoy the shortness of short hair while also being able to work with long hair, but not too long.

Classy hairstyles for medium length hair are plenty. However, the more popular ones are always the classic and simple ones. Take a look at our first hairstyle. It’s just the kind of classy medium length hairstyle that you just achieve with your fingers, and then lock in with a little hairspray. Nothing too complicated to do, but always a little fancier than your average hairstyles for men.

Classy Hairstyles for Medium Length Hair # 2


Classy hairstyles on medium length hair should look naturally sexy and appealing, too. What’s the use of having all that hair if you’re not going to use it to your advantage? Check out this tousled and messy but very sexy hairstyle on our guy here.

The hair is long at the back and grazes the collar of the shirt just very lightly. The top hair falls over the eyes in such sexy fashion that you will feel like a leading man in a romantic movie every time you move your head. This hairstyle will naturally look awesome on guys with straight to wavy hair. And dark hair. Nothing looks more dramatic than slick and dark-colored hair hitting the lights.

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Classy Hairstyles for Medium Length Hair # 3


Classy hairstyles are always timeless and sophisticated. You can wear them with just ripped jeans and a wife beater and you will still look like a million dollars (okay, that may be a bit of a stretch, but you get our drift).

Men have been wearing this kind of medium length hair for decades. We just watched Cocktail again, and Tom Cruise was wearing this kind of haircut, and it still looks great! It just goes to show that classy hairstyles won’t make you cringe years later when you dig up old photos or videos from a certain era.

How do you style a hairstyle like this? You just apply your favorite styling product, preferably one that does not have a lot of shine or stickiness, because you want your hair to look soft and natural while still held in place to last the whole day. With a comb or a brush, you just style it and follow the natural direction of the hair.

Classy Hairstyles for Medium Length Hair # 4


Classy hairstyles also mean the classic pompadour. Thanks to the growing population of hipster fans, more and more men are discovering the wonders of the pompadour. Big hair, long hair, short hair, or little hair — a pompadour is possible if you just know the right way to style one.

The pompadour will look even better on a short on sides and long on top haircut. The short hair at the sides provides a really dramatic effect on the pompadour on top of the head. And the longer your hair on the top is, the bigger and the more stylish the pompadour becomes. You can do it with an undercut, or a fade haircut. You can also pair it with some impressive facial carpet and a really cool outfit.

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Classy Hairstyles for Medium Length Hair # 5


Curly hair blowing through the wind is just the stuff that women go crazy about. If you can get your curls to behave a certain way, we see no reason why you will grow old alone. Really.

Curly hair on a short haircut is challenging enough. More so on medium length hair. Challenging, but not impossible. A good way to make sure that your curls always look great is to use a really good shampoo and conditioner specifically formulated for curly hair. This can help reduce frizz and dryness, and it can give your hair the natural softness and shine that it needs. A good leave-in conditioner is also helpful for extra humid days to keep your curls looking good and moisturized.

Classy Hairstyles for Medium Length Hair # 6


When you have medium length hair, you can wear it long and shaggy, with a very don’t-care-about-the-hair attitude. Just keep it long and straight, and let it fall naturally all over. Classy hairstyles like this need not look perfectly combed or polished, because you still want a little texture and a little mess, especially on the top hair.

It’s a great hairstyle for guys who have straight, thick, or fine hair. Getting some layers or textures on your hair will also make it look interesting and more styled. Keep the sides short and the top long so that the hair looks natural and not like it’s just placed there awkwardly at the last minute.

Classy Hairstyles for Medium Length Hair # 7


How can we forget classy hairstyles that will look great on the perfect gentleman? This is an example of a medium long hairstyle that will look neat when worn natural or slick. It suits naturally straight or wavy hair, as well as fine and thick hair. Even men who have thinning hair or receding hairlines.

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To achieve this kind of effortlessly fashionable and stylish hair, get a really good haircut that’s short on the sides and a little longer at the top. This will give the hair a nice shape, even on bad hair days. What’s great about these kinds of classy hairstyles is that you can also use your fingers to comb through the hair, and you will get a completely different look as well.

Get creative with these classy hairstyles. You can actually wear a different hairstyle every day for an entire week. Just switch it up every now and then so you always look like you’re wearing brand new hair each time.

Medium Hairstyles