I have a cowlick problem so I cut my hair real short. #6 on top, #3 on the rest. I'd like to grow my hair out but dont want to look like an older homeless guy. Older guys dont look right sometimes with longer hair. I'm not in transition at the moment. The best option would be a hairstyle that could be manly or womanly. But, a nice medium or longer men's style is good too. I have all my hair. Any recommendations?

Also, when it starts growing out the cowlicks will look awful. Any good products to keep them under control?

I'm not sure how old you think middle age is, but see number 6 and 7 here:
https://www.liveabout.com/cool-haircuts-for-men-over-50-2326745
As a start for when you are growing it out.

The best idea I have for cowlicks is get used to using a blow dryer. Hair will pretty much stay in place if you dry it where you want it. Without a perm, my hair has just enough wave that it misbehaves at the ends. I towel dry, use a hair dryer to get more of the moisture out then using my hand and a curling brush I do the final shaping while removing the last of the moisture. After that, a little touch up with an open tooth wet brush and I am done. If you want it to last all day, you would give it just a little hair spray but I don't mind a little messy look as it softens my features.

As for styles, my standard place to look is Hair Finder

Sometimes you have to be patient and cope with a period in which your hair will look bad. Like me, I either have it really short or long. Medium lengths don't look good with my hair. I went through that period with the lot of gel and hair straightener. I had to straighten my hair every day, which was time consuming, but it made it look decent and more delicate, maybe feminine.

With those tools, my hair grew long enough so that I could tie it.

I suggest you use a similar strategy. Gel, hair straightener, maybe a headband until you can tie it and then it will look good. Take a look at ancient Asian male hairstyles. Long hair tied in different ways was very common in males. You'll also have a lot of fun trying the huge amount of ways to tie your hair. From simple, masculine styles to more crazy, complicated ones, and more delicate, feminine and even ambiguous.

Yep, I had to deal with this.  The answer depends on your hair type.

Mine is very curly, I am half Welsh.  Medium length is great for me if I want to do a Bozo the Clown imitation but I prefer to avoid that.  (I'd get the wrong kind of dates).  I tried taming my hair with "product" which is an overpriced way of saying "stuff" only to have it go literally haywire when I traveled to more humid countries or whatever.  At the point I was wearing snow hats in the summer I realized there must be a better way.

So I did a reverse perm and it was awesome.  It's called a Brazilian Blowout and I have also had the more extreme Japanese Hair Straightening procedure.  Both have worked great for me during the past two years but I have heard horror stories of people wrecking their hair with aggressive chemicals... this is not the time to be using Groupon or some DIY kit from eBay.  In my particular case I believe these procedures were better for my hair compared to dumping stuff on and frying it daily with a flat iron.  I have gone several days just brushing, or a very light touchup with a flat iron and my hair usually looks like it does in my current avatar.  As my hair is growing longer I need to straighten it less - it now sits the way I want. 

There is really no way around a awkward stage when you grow your hair out. Cowlicks make it worse. Cowlicks can be tamed by blow drying and a good freezing spray. 2 really good ones are Matrix vavoom freezing spray and Tigi bedhead hard freezing spray. I use both at work and they are great. Spray the cowlick with the freezing spray while your hair is still wet. Aim the blowdryer at the cowlick in the direction you want it lay. Use a ventbrush to brush it down as you dry it. Use more freezing spray as needed. Once the hair is dry and the cowlick is cemented down, use a bristled hairbrush to very gently brush through the freezing spray on the cowlick. You just want to break up the freezing spray a little so you don't have a shiny hard spot in your hair. There will be a period where the cowlick is not long enough to lay down. During that period all you can really do is wear a baseball cap. Once it's long enough to work with just keep it neat by blow drying it smooth and using a medium hold hairspray on it. Don't use the freezing spray all over your head. Your hair would look like a blob of plastic if you did. As you grow it out keep your neckline trimmed. It will help make your hair look neater.  If you grow it out long a ponytail is acceptable for an older guy. But don't do a manbun. That's for younger guys, and even on them it looks retarded.  In my opinion.

I hope some of this helps.

I'm watching this thread closely.  I have lost a lot if my hair but am fighting like crazy to not wear a wig.  So I'm looking for a style that I can grow out a bit and be femme, and not look ridiculous.  Suggestions are appreciated.  I'm 47, BTW too.

A bowl or wedge cut/Dorthy Hamill is a good intermediate cut and it works with hair loss and brows. The hair is parted at the back of the head and pulled forward so it will cover a number of issues. In my case, I don't intend on having FFS so my forehead needs to be covered.

Should you want longer hair, you have the bangs in place and can grow the sides out. It's also possible to part it on the sides for a more masculine look should you need it.

Thanks Dena, that haircut gives me hope.  I also found this link which show layered looks for thinning hair in women.  I have much thinner hair than this, but here's to hooing:)

https://www.pinterest.com/pin/359584351470921973/

Lot's of good info, I can definitely rock these two styles. I have all my hair, it's thick and no thinning. I'm more partial to #7.

Quote from: KarynMcD on August 31, 2017, 01:31:30 PM
I'm not sure how old you think middle age is, but see number 6 and 7 here:
https://www.liveabout.com/cool-haircuts-for-men-over-50-2326745
As a start for when you are growing it out.

I don't know what you do for living, but if you can wear a bandanna all day, your hair won't be visible under it. It's not that unacceptable for a guy (as long as it's not pink )


Sent from my iPhone using Tapatalk

Quote from: KarynMcD on August 31, 2017, 01:31:30 PM
I'm not sure how old you think middle age is, but see number 6 and 7 here:
https://www.liveabout.com/cool-haircuts-for-men-over-50-2326745
As a start for when you are growing it out.

Cool! My hair is currently kinda like #6/#7. I like the Jackson Browne look, so I'm growing my hair out more but not quite as long as his hair length. I grew my bangs longer to hide my cowlick, which is a big one. It's not even noticeable now. I tried different products in my hair but couldn't get a good look with any of them (yuckie stuff). Lots of women wear short hair, and before mine grew out more I was still confident going out as fem. I finally settled on a natural look with no product. I don't want to look too made up or over the top, so it works for me. Using a blow drier to style it a little bit works well. I use 'Just for Men' to keep the grey out - I tried women's hair coloring and it didn't work as well. When my hair was shorter I tried a wig, but I got a bunch of double takes and stares with it on -- I wasn't passing -- yikes! Even the best wigs still look like a wig. So, I shelved the wig and a natural androgynous-non-binary style is working. Everyone over 50 like me may have some balding so they don't have that option. I'm blessed with good hair, so they say. I guess it depends on how fem you want to go. You'll find your groove. Good vibes!

Quote from: KarynMcD on August 31, 2017, 01:31:30 PM
I'm not sure how old you think middle age is, but see number 6 and 7 here:
https://www.liveabout.com/cool-haircuts-for-men-over-50-2326745
As a start for when you are growing it out.

I see a lot of older bikers rock something like #7, where it might be the same length but they slick it back. I wonder if that sort hairstyle could be easily styled as women's hair? Then I could slick it back for work, and then brush it normally for women's hair. What do you think?

I'll be watching this one. An ambiguous hairstyle for the next 3-6 months would be nice. Long term I want to let it grow out long. My hair is naturally quite fine, straight, and black and tends to stay where its put when it gets longer. However, with a little thinning and receding at the top I suspect I'll have to manage the fringe rather carefully.Wigs, unless they are really expensive in my opinion look a little wrong. I hope I don't have to go down that road.

I've figured out how to keep my cowlicks down. I have Woody's Mega Firm Gel. I dampen my hair and use the gel. Then, where my cowlicks are, I push them down with my fingers and hold them for 30 seconds or so as the gel is drying. I keep repeating if they want to come up. When the gel is dry enough, they stay down.

Some Pixie cuts, and some other short hairstyles, can look quite androgynous, others, oh so feminine.

Those styles may work well for those transitioning or who want to be, those who are gender fluid or androgynous, and those that simply prefer the looks of short natural hairstyles.

Since I've started to grow my hair longer again, I've noticed a cowlick that I had when I was a kid. 
But to answer the question.... I talk to my hairdresser about longer styles (she is unaware at this time) and I showed her a pic of a guy with an androgynous hair style similar to Lisa Rinna's (on housewives) somewhat pixieish hair.  She thought it would look good!  She told me as it grew longer, don't comb it or brush it, except to brush it straight back all over, then let it fall forward on its own, laying where it will.  Mine sticks straight up and stands on its own till it falls forward, which looks close, but shorter, to what I want.
My hairdresser says the weight of my hair will counteract the cowlicks that form from my wavy hair.  My Farrah Fawcett curls are starting to show.  So I may go with that.

If you want a slightly longer style as compared to Pixies, you may want to consider the varieties and lengths of Bobs and Pageboys hairstyles.  Some of these styles could look adrongynous, and workable for those not yet transitioning or are in transition. 

But, after your hair grows out to cover or hangs down over the sides of your cheeks, it is difficult for your hair to not look feminine.   You can only tuck in so much of your side face hair behind your ears.

Yes, we have all seen dudes with medium to long hair and they still look like guys... they just typically do not have feminine hairstyles.

Chrissy

My hair is naturally wavy, and cowlicks were a problem.  Once it got too long to keep out of my face, I ponytailed it with silicone rubber bands made just for that purpose, available at Walgreens.

I pinned the out of control left side back with a brown barrette.  No one ever said anything.  Just grow it out and don't worry about it.  Even Blackbeard used to put ribbons in his hair (when he wasn't putting lit matches in there).