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So, I kind of feel like nature is catching up to me, and the long hair I've always liked is looking less "cool" and more "creepy uncle". Anybody have any advice about how to find what looks good? I've searched around the web, and every site is roughly the same. "Is your face shape X? Then try this really generic hair advice that really doesn't say anything useful!" I've also tried asking multiple stylists, and they always try to shift it back on me because they don't want to be responsible for a bad haircut.

Any advice?

Try making a picture with your hair out of the way and ask someone to Photoshop some differ styles on you?

Aren't there some apps out there that you let you try out haircuts with an uploaded picture? Too lazy to go look myself. Also, I have shaved my head for more than 10 years, so I might be out of touch with the whole hair thing.

Whatever you choose, you'll always be a creepy uncle in my heart

But for real it seems like any variation on a fade seems to be in right now. Maybe a med/high fade with a textured top.

There should be quite a few sites out there that you can "try on" a hair cut. Hopefully free websites

I find that those generic comments about face shapes aren't super helpful. A lot more than the shape of your face goes into what hair style suits you.

When I was done with my super long, over processed, damaged hair I just went in one day and had 14 inches of it cut off. My hair dresser wouldn't cut more than that and insisted that I go to a pixie in stages because she had many clients freak in the past if the went too drastic in one go. I don't know how long your hair is now, but it was good advice for me at the time. Doing it in stages let me get used to having less and less hair.

Now the funny part is that I'm totally growing it out again. The best that I can with my infusion getting in the way. Now that I have a pro colouring my hair and I'm using high quality hair supplies, my hair is in really good shape so I can' have it long again without it looking like straw.

(I realized that this isn't very manly advice! Sorry!)

As someone whose hair has decided to passive-aggressively fuck off, I hate that you have options.

When I was in the military, I would get the most aggressive flat-top high and tight I could get, cutting the hair into a horseshoe on top.

Now, my hair says "Oh, you spent all that time not wanting the top to get longer, so we decided that we'd stpo growing it all together."

If I got without a haircut for a month, I look like fucking Bozo the Clown. :/

Officer_Charon said:

If I got without a haircut for a month, I look like fucking Bozo the Clown. :/

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If I go without a hiarcut for a month, I....pretty much still look like I got a tonsure.

So you still rocking the creepy uncle?

I just cut it shorter, but mostly kept the same style. It's decidedly less Lester the Molester.