Should I Cut My Long Hair?

6 min read

SHOULD I CUT MY LONG HAIR?

A Personal Experience (& "Decision" Guide) Going from LONG to SHORT Hair from Our Creative Director

Anybody that’s ever grown out their hair understands that it takes a bit of mental stamina and patience to do so. First, you need a relatively good set of hair to start with, then you're willing to dedicate months (years in my case) to grow it out, and ultimately you'll suffer through the various awkward phases that come your way - 

All for the prospective glory of letting the flow rage (yes, that's a thing).   

Then one day you're ready to chop it all off and shave your head faster than Britney Spears having a meltdown.

What gives?

You survived this long journey to luscious locks (and let's be honest, you're the envy of every man, woman and child who sets eyes on you) - and now you're start asking yourself "should I cut my long hair?". 

If you haven’t hit this stage yet, trust me, it’s coming.

How do I know? Well, once upon a time my hair was down past my shoulders.

What I thought would be a year long experiment capped off by a donation to Locks of Love, quickly turned into 3 years and a more than mild attachment to my new long haired identity.

While I was able to make it to the three year mark, it was somewhere between year 1 and 3 when I really started questioning if I wanted to keep the hair long or just cut it short.  It didn't help that my friends, girlfriend, and family kept asking too.

By now you’re probably asking yourself the same question, and chances are you don’t know anyone who can offer advice from their own experience. Well fear not, I’m here to share my personal experience to "guide" you in deciding whether or not to chop off your lettuce.

SPOILER ALERT: I think you should cut your long hair!

MY TOP 4 DON'TS...

1.  Don't Cut Your Hair For Someone Else

This one should go without saying, but don’t cut your hair to try to please anyone else.

I don’t care if it’s your girlfriend/boyfriend, your mother, your grandmother or your employer - you’re the one who grew out your hair, so you’re the one who gets to ultimately decide what to do with it.

As long as you’re confident with it (and you bathe regularly) you should be able to wear your hair however it makes you feel comfortable. This is ultimately your decision so own it!

2.  Don't Get An Undercut

For the love of God, whatever you do, DO NOT get an undercut!!!  I cannot stress this one enough.

I know it sounds tempting; what’s not to love about cleaning up your neckline, taking some weight off the back and making it look more “professional”?

I promise you....

One of the best parts about having long hair is not having to worry about getting a haircut every 3 - 6 weeks. 

As soon as you get an undercut (or even low fade) you lose that convenience.  Your hair will go from 'easy to maintain' to 'high maintenance' from 0-100 real quick.

Cleaning up the neck line totally fine, but once you go above the neckline you'll regret it.  Trying to grow your undercut back out to the same length as the rest of your hair is a disgustingly frustrating process and annoying.

3.  Don't Shave It All Off

You’ve spent months, if not years, growing out a gorgeous head of hair that any stylist would love to have a field day with. When the time comes to part ways with it, walk into a salon and get a proper haircut.  

Stick with scissor cuts and stay away from clippers.  

Since you’ve got more hair to work with, you can leave with a unique hairstyle that most people can’t pull off. You can always go shorter after a few weeks if you decide it’s not for you, but you can’t add more once you cut it off. 

4. Don't Delay The Inevitable

If you're trying to decide whether it's time to cut your hair or not, then it's probably time to cut your hair!

 "Should I cut my long hair?" is the equivalent of "Should I stay in this relationship that's going nowhere and is likely going to end someday?"

Just cut'em loose! (pun totally intentional)

The longer you drag out the internal debate, the longer you’ll hang onto a hairstyle you’re probably already over.

Don't worry there's also a positive to a clean break - the only way to know if you truly want long hair or not, is to cut it all off and see if you miss it. So the sooner you cut your hair, the sooner you’ll silence the endless internal monologue.

Most likely, you'll be happy with your decision!

But if not, it’s easy enough to grow it out again (the trick is that you do nothing). The only difference will be that this time you can rock your long hair with complete confidence because you’ll be certain that you were destined for long hair.

Now that we’ve handled what not to do during this dilemma, let’s look at what you shoulddo.

MY TOP 3 DO'S...

1.  Just Do It

As we already mentioned, if you’re asking whether or not you should cut your hair, then you probably already have your answer...

Luckily there’s nothing to be nervous about since there are no shortage of hairstyles and products (*cough* Mister Pompadour *cough*cough*) to help you find a new look that’s right for you. Take a few days (or weeks) to enjoy your glorious long locks one last time, then let the shears run wild.

2.  Donate Your Long Hair to Charity

While you may still love having long hair, there's a lot of people in need who could really benefit from your majestic mane.  Instead of letting your flow go to waste, why not let your long hair truly transform someone's life?

When I cut my long hair I ended up 12" to a good cause via
 Pantene Beautiful Lengths.   While that program isn't around anymore, there are still plenty of other organizations you can pledge your hair to:Wigs For Kids,Locks of Love,Hair We Share &Children With Hair Loss to name a few.

For me, there was no better feeling than knowing that a 'part of me' was going to make someone's life better, especially since I've had multiple people in my family affected by cancer (and the hair loss that comes with it).

I CHALLENGE YOU!

If you cut off your hair and donate to charity, then please send us your photos and we'll send you a FREE Styling Product of your choice to get you back into the routine of styling shorter hair again.


Another option is to participate in one of theSt. Baldrick's Foundation’s head shaving events. I know I just told you not “shave it all off”, but these are slightly different circumstances since you’re doing it for a good cause.  Still make sure to donate your lock hair first - and then rock that shaved skull like nobody's business.  

3.  Embrace Your New Look

While you might just be getting a few hairs snipped off, you’re about to get a complete overhaul in the looks department. Make sure you own it!

People love a good transformation, and they especially love someone who’s confident about their new look. Even if you decide to grow your hair out again, enjoy the short hair while it lasts.

No, you won’t be able to hide your bedhead by tying your hair back in a bun anymore.

And yes, you will have to get your haircut more often than you’re used to (unless you already botched that whole anti-undercut advice).

But how amazing does it sound to not have to deal with brushing out tangled hair?

Or accidentally snagging your hair in zippers, velcro, jewelry and sunglasses (all true stories).

And don’t even get me started on the difference it in how long it takes to dry your hair!

For me, it's a lot more enjoyable sporting a shorter textured hairstyle rather than dealing with long hair.

So focus on the benefits of the short hair, don’t care lifestyle and fully embrace your new look.

The Wrap-Up

Well there you have it, my personal Do’s and Don’ts when it comes to deciding if it’s time to let go of the long hair. I’ve kept this list fairly simple in the hopes that you won’t over complicate the process, but leave a comment or reach out through Instagram if you have any questions.

If this post helps you take the proverbial leap and you decide to cut it off, then we’d love to see your hair transformations - just make sure to include a link to the photo(s) in the comments section!

Thanks again for reading and I hope you enjoyed!

Robert, Creative Director

Robert L
Robert L


Leave a comment

Comments will be approved before showing up.


Also in Expert Advice - From the Blog

Paste, Pomade, and Clay...What's the Difference?

13 min read 37 Comments

Do you know the difference between a hair paste, pomade, or a wax? Learn about the different kinds of hair products for men. Who knew there was so much variety?
Read More
What Does Your Hair Say About Your First Impression?

3 min read 3 Comments

Simple Fact: Looks Matter!  Your look is your biggest asset for a solid first impression.  Whether you're out with your friends, at the office, or on a date,your hair should impress!  Let’s start with what your hair says about you...
Read More
Men’s Winter Hair Trends

3 min read

With the winter around the corner, it’s a good time to freshen up your look. For most guys, this starts with your hair (and maybe a new Tinder account) to swing into the new year. So, the first thing to consider is this: how updated is your hairstyle?
Read More