The iconic “short on the sides, long on top” men’s hairstyle is a classic look that’s not going anywhere, at least not anytime soon.
The contemporary version of this hairstyle – the undercut – has been all the rage for the past few years. If you’ve been rocking a short undercut for a while and are thinking about growing your hair out, this post is for you.
Here’s the thing: I love the undercut. The disconnect between the top and back and the extra length on top make it a really cool haircut that flatters most men.
It’s also a very easy haircut to achieve since most barbers can do an undercut in their sleep.
But the undercut does have its downsides…
It requires regular haircuts (at least once a month), and it looks really bad if you don’t style it with product. Plus, it gets a little wild when you run, swim or workout.
So you might be thinking about growing out your hair a little bit or looking for a lower maintenance hairstyle. Or maybe you just want to try something new.
And why not? Many men look great with longer hair. It can even be easier to manage than the disconnected undercut (less haircuts, less shampoo, fewer showers and less product).
But growing out your hair from an undercut – or any super short haircut – is a long, awkward process. The sides and back will be way shorter than the top – especially the front – so you’ll need to go at least a couple of months without a haircut before you get it cleaned up and evened out.
Once you grow it out a little and get it cleaned up, you’ll have a versatile, medium length hairstyle that’s connected at the sides and back and has plenty of room to grow.
See Also: How to Cut Your Own Hair
This hairstyle is super easy to style with a classic side part. The great thing is, when it’s this long, you can actually brush it straight back instead of trying to get that perfect swirl around the crown of your head.
The result is a classy, mature side part that makes you look like you’re heading to an exclusive party at Jay Gatsby’s mansion.
Here are two ways to style medium length hair:
The Medium Length Side Part
Start with damp hair. You can towel dry or blow dry your hair after a shower, or just wet your hair under the faucet and towel dry to remove the excess water.
Comb or brush your hair straight back, away from your face, on the top and sides.
If you have thick hair, make sure you get all of the knots out.
Push it all straight back, including the hair on both sides of your head.
Grab your favorite pomade, crack it open and take a nice long whiff of the masculine fragrance. In this case, I’m using Old Spice Pomade, which has a pleasant, mild scent.
Scoop a healthy serving of pomade from your jar, and spread it evenly across the palms of your hands.
Coat your hair with the pomade, making sure to push it in all directions so each side of every strand has product on it.
Now, choose your part line, stopping 1-2 inches short of the crown of your head. When your hair is this length, you can actually comb the rest straight back, rather than trying to navigate the natural swirl of your crown.
It should look something like this:
It might look a little too slick and shiny at this point, but it’s going to look awesome when it dries, especially if you’re using a matte pomade like I’m using here.
Notice that I’ve parted my hair to the right. I’ve always parted it that way, as long as I can remember (well, at least since middle school when I parted it right down the middle…WE DON’T TALK ABOUT THAT ANYMORE).
With medium length or longer hair, you can actually part it both ways, and you’ll get a slightly different look.
Parting Your Hair the Other Way
If you’ve always parted your hair to the right, try parting it to the left. You might be pleasantly surprised!
For most guys, parting your hair the other way will lead to a slightly different (and maybe fuller) shape.
It might take a little extra product the first few times, but eventually your hair will become trained to part that way.
The process is pretty much the same.
The result is just a little different, and I actually really like how my hair looks when I part it to the left.
It has a nice shape to it, and I think it makes me look a little more mature and even older (in a good way).
Will you grow your hair out?
If you’ve been thinking about growing your hair out, I encourage you to give it a shot. Worst case scenario: you hate it and get it cut.
But remember, it’s going to take a little while, so be patient! And if you’re in the market for some new (very affordable) pomade, check out Old Spice on Amazon.
Thoughts? Questions? Leave a comment below!
Can I just say that when you part your hair on the right you look more like a celebrity. It shocked me what a difference a hair part can make but if you’re still parting it to the right please keep doing it! (Your choice of course, don’t let me sway you) But to me personally you look so much more inviting and friendly.
i’m a new subscriber…Thanks for all your updates..but this haircut looks good…doesn’t work for curly or wavy hair. Those of us with curly or wavy hair have surly tried a few hundred times to get it look like that. Any ideas for curly hair??
Great post. I read a really interesting article recently (I could probably find it but I’m too lazy) about mirror effects and how this can drastically change perception (they used Abraham Lincoln portrait, straight and reversed / mirrored as an example) both in how you see yourself and how others see you. I think I remember correctly that the vast majority of guys part on one side (their left I believe) and that if you decide to go with a part on the opposite side it will definitely change the way people see you due to this underlying familiarity with seeing most guys having it the opposite way. I don’t think their is a right answer, but I found this interesting.
Great post Brock! I’m in the process of growing it out now and have only trimmed the edges for 2-3 months now. I am trying different ways of getting the final look but it’s not quite long enough for the hair near the crown to stay down. I find I had to blow dry it to the look, then use product to hold it there. I actually use the old spice pomade as well!
Please please….when are the beards and mustaches going away?? Men look so dirty and very old no matter how neat they trim them. My son started growing his beard at age 25 to cover a double chin and he became old. My hubby is so ugly with his grey brown beard. Most men who have gray beards look so old and it looks dirty. I know it is an easy way out of shaving and a lot of women like it but I guarantee these men would look younger without it. Same with long side burns. They remind me of someone who thinks they are cool but are really tacky.
I like the clean look too, but then again, I don’t really have a choice. Can’t grow a beard to save my life!
That is a good thing! When you are 70 (I know it is a long way off) you will look much younger and can get younger partners too!