I’ve decided to grow my hair long. For the past 20 years I’ve rocked a basic high and tight, as seen here, third pic down. Now I’ve decided to aim for something more like this guy.
Is there any product, styling regime, tonsorial schedule, or any other information I may need in order to manage the transition? This is a completely new direction for me and I’m a skosh intimidated!
First, quit getting haircuts. You will need an occasional trim to even up the ends. Shampoo daily with decent quality stuff. If you’ve kept it short the last 20 years, don’t be surprised if it grows out curlier than you think it will, especially if puberty was in or near the start of those 20 years.
I was pretty much where you were about 4 years ago. My hair is now about halfway down my back, so quite a bit longer than you and Theoden.
california jobcase pretty much nailed it there in Post 2. I actually haven’t had a cut in as long as I can remember, but I really should go in for a trim. And as far as it growing out curly, that definitely happened to me. My hair was always straight. but as soon as it got to my shoulders it started curling. It stayed like that until it was long enough that the ends were well past my shoulders, and now it’s back to being straight again.
You’ll need to use more shampoo than you’re used to, and you’ll have to spend some time every day actually ‘doing something’ with it, but really the key to growing long hair is simply to let it grow long 
You will want to get it all cut off several times a year. It will suck having to deal with it constantly. Get a couple different shampoos and rotate them. Get some leave in conditioner so it doesn’t get too puffy and fluffy. Get ball caps and sweat bands, there will be days you don’t want to deal with it.
Goodness get a good looking hat not a ball cap or sweat band.
I used gel products on my hair while it was in the in-between awkward looking stage, but I was growing mine out from short to pony-tail length.
It’s not too late to change your mind.
Use a mild shampoo. Like baby shampoo. You don’t want to dry out your hair because then it will become brittle and break off. Use conditioner.
Eat healthy to grow healthy hair.
Be patient.
Well, it’s going to take a while. It will spend some time between short and long where you can’t control it. That’s like your hair’s teenage years. Actually it’s not that bad. Just spray on some of that hair goop your wife has to hold in place. I prefer mine long enough to tie back. If I tie it up while it’s still wet it dries pretty straight. If I let it air dry I get varying effects from lion’s mane to Jesus (scruffy old Jesus now).
Off the top of my head:
Get regular trims for split ends.
Don’t ever brush or comb while wet.
Be careful how you scrub when you lather up. There’s an art to getting shampoo evenly distributed without getting mass tangles.
It will look like crap while it is growing out.
Depending on how thick/fine or straight/curly your hair is it may take a while to dry. This is something you’ll get a feel for.
In windy weather, wear a hat or something to contain your hair. Unless you like combing out tangles.
Don’t operate a vehicle in Las Vegas. The police will arrest you for probable cause based on your hair length. Damn hippies!
I’m a girl, if it matters, but I’m going through the same thing. I’m currently growing out my hair from a short haircut I got a few months ago, and I’m at the awkward middle-length stage. I don’t think there’s a big difference between how girls and guys grow out their hair, but you can disregard this post if you disagree.
I had grown out my hair for my entire life from age 10 to 27, and it was curly and frizzy the whole time. I was quite surprised after the short cut I got, because it ended up being straight and smooth! So, as mentioned above, don’t be surprised if it gets curly or wavy as it grows out.
To cope with the transition, I’m using mousse and headbands. I take a shower in the morning and wash it–no conditioner needed yet. Rub dry with a towel, although as it gets longer I will eventually have to resume avoiding this step (rubbing long hair with a towel is a big no-no, for curly hair at least). Then I put in mousse and slick it all straight back with a boar bristle brush (this ensures maximum smoothness and straightness later on). After it air dries, I brush it all forward to get the mousse residue out–dry mousse will flake, so bend over or else your shoulders will look dandruffy. After that, I just brush it to style it how I like. Sometimes I do a center part, sometimes a side part. Sometimes I brush it all forward and do sidesweeping bangs (kind of how Justin Bieber and that High School Musical kid style theirs). On bad hair days I use a headband–you could just use a ballcap instead. I don’t have nearly as many bad hair days as I did when it was long, though.
Once it gets long enough, you can pull it back into a low ponytail when it’s wet. Try to avoid brushing wet hair too much, especially long wet hair, because that leads to breakage. You can use a wide-toothed comb with rubberized tips to detangle it as needed. If you like to brush it though, get a boar bristle brush because they don’t damage your hair like the cheapy plastic nubby brushes do. My brush is honestly the secret to my style–I can change hairstyles in the middle of the day without wetting or adding product, because the brush is so great.
The nicest long hair I’ve ever seen on a guy was a friend of mine who basically did almost nothing to it. He would wash it in the morning, put it in a ponytail, and go. When he let me brush it, it was sooo luxurious and beautiful. Good genes, of course, but the fact that he never brushed it or heat-styled meant he didn’t have any breakage or split ends to speak of.
That’s actually a good rule of thumb right there - if you want long hair do as little to it as possible. Don’t blow dry if you can avoid it, don’t dye it, bleach it, etc. Keep it clean and brushed and don’t cut it (An occasional trim to avoid raggedness is OK)
I disagree with the advice to quit getting haircuts. Take the end picture to your hairdresser and let them know that’s what you’re aiming for. They can then style and trim your hair in a way that you continue to look decent whilst you’re growing it out.
Don’t go bald. I had long hair, but I started to go thin on top, and it looked really bad. Especially when wet. So I dramatically shortened it.
I’m guessing you’re middle aged (45+) or close to it.
Bear in mind that nothing makes a middle-aged person look old more than long hair, unless it is in perfect, non-graying, non-balding condition. Even then, the contrast between perfect hair and the lines/wrinkles in your face will make you look older than you are.
I am the voice of experience here.
(If you’re still in your 30’s and can carry it off, go for it, but be prepared to cut it off again later when it starts to make you look bad. You may need an objective 3rd party to help you not go too far past that point.)
Roddy
I’ve been shaving my head each day for the past year, but for about 30 years before that I had long hair.
I never went to a barber. I combed everything straight back and used small rubber bands for a pony tail. If the tail got too long for comfort, I’d hack six inches off with scissors. Each morning I shampooed. Pretty simple.
I rarely went without a hat (not a ball cap) during the growing out stage … occasionally used some kind of goo to hold it combed straight back. It’s just gonna look ratty for a while and trying to keep it trimmed to look less ratty will prolong the process.
It’s been maybe five or six years of pony tail now, with just a yearly trim of a bit off the bottom.
Lather your scalp when you wash and not so much the ends.
I’m silicone and SLS free myself much of the time, but the ends rairly need touched. Actually, much of it does not need touched.
I’d invest in some metal-free, covered elastics if you’re planning ponytailing it.
(Caveat: I’m a lady at hip-length.)
Here’s another point to keep in mind. Some peoples’ hair will never get past a certain length. Exhibit A: my scalp. My hair is very fine and splits or breaks if anyone even looks at it funny. Even with very gentle handling it’ll never be waist length. A few strands have made it to my waist when I let it get that long, but past shoulder blade length it gets very straggly. So I keep it trimmed.
I mention this for two reasons. First to say how envious I am of persons who are able to grow their hair that long, grr! Second, to point out that if your hair has for a long time been cut very close to your scalp you may not really know its texture and how sturdy or fragile it is and you’ll need to learn what sort of handling it needs.
When I wore my hair very long a few people told me the same thing. I always pointed out that I didn’t give a fuck. Worked for me.
