I have fine, very straight hair that I gel to the max and blowdry into the “middle-aged lady short, disciplined hairdo.”
My hair would have worked really well in the 1960s and 70s when long, straight hair was the rage.
The complicated styles of the 1940s would have been really difficult, as would the complexities of a beehive in later years – I’d have used two bottles of Aquanet a day in order to lacquer my fine hair in any semblance of curled up-do.
I would have made for a shit hippie, but did great in the 80s. My mother snickers any time an ad stating “this shampoo will give you great volume!” comes up on the TV; I need extra volume like I need extra toes.
Twenties? Maybe. Just anything with really short hair, so flappers or pixies. Not necessarily because it makes me look awesome or anything, but because it’s the easiest to keep up with that makes me feel better about myself.
Also, I now need a haircut.
I’m balding down the middle, so if this were the 70s, I’d look like Jerry Ford. Not necessarily a great look, balding with longish hair in the back and sides.
Luckily the Matt Lauer-look is acceptable these days.
Luckily, the Uncle Fester look “works” in any era. A pain to maintain with bronze razors, I’ll grant you.
The term I use when thinking about my hair is squatchy. And right now it’s too short. I have to iron it daily just to look like a sane person. So I guess the 60s or 70s…eras where it would be okay to look wild, yet also having access to a flatiron in case I needed to go amongst the squares, man.
I would like to see someone try to get my hair to do one of those smooth 40’s rolls. 
My hair is much like Ilana Glazer’s hair but maybe thicker (it’s thick, I can’t tell how thick her hair is). A mess of thick dry curls.
If I don’t put any product on it, I can do an excellent white girl afro. My dad was rockin’ the white guy afro in the 70s, so I’m sure that is where I’d fit in best.
Any other era, I’m sure I would have been beaten repeatedly with some form of hot iron.
My hair is wavy and grows straight back. When I was younger, I could manage a part, but somewhere around 4th grade, it decided it was done with growing sideways. I’m white, but my hair does a good impression of a 'fro if I don’t keep it pretty short… so I have a style that would pretty well pass muster for a guy in any era. In some time periods, I might have slicked it back with gel, but I prefer to just keep it short and combed back.
My hair is very fine and very straight and does not grow long. In days when women were supposed to have long hair, I would have had to have a wig or keep it under a bonnet or a veil. I do best with a 1920’s bob, I guess. It doesn’t grow much longer than that, and I look awful with really short hair, like a pixie cut.
I’m a guy with slightly wavy hair and a businessman’s cut. I be timeless!
My hair is thick and frizzy and has a mind of its own. The more I try to do with it, the worse it looks, and it won’t hold a curl at all. For most of my life I’ve worn it either long and straight or in a pixie, which is my favorite style once I beat the (at last count) 4 cowlicks into submission every morning.
By far the worst style for me was “Mall Hair.” When I started jr. high in 1988 my mother and sister decided I had to get a perm like all the other girls. The stylist had to use such strong solution that it burned my scalp. The hair was breaking off and falling out. That did not help the frizz factor at all. Add to that the fact that the style looked horrible on me and I hated it and couldn’t be bothered to even try to maintain it… it was really, really awful.
By 8th grade my hair was such a wreck that I just got a pixie cut, which I was much happier with, but since I weighed about 100 lbs and never had much of a figure I had to put up with people thinking I was a boy so I grew it back out in high school.
About the same. Short and parted on the left. I suppose for some eras I could slap some oil in there to slick it down but the haircut itself should last me though the 1900s at least.
My hair is like ZipperJJ’s. It was out of place in the late sixties/early seventies when long, straight hair was in. The late seventies Farrah Fawcett wings were not suited to it either. Maybe that cup of coffee in the mid-seventies when the natural look was in.
My beard would never work in the 70s, it would mean I was a hippie. I could have one, but it would be taken as some sort of political statement. And it would be even more unacceptable earlier in the 20th century, when anything other than clean-shaven was unthinkable. I’d have to go back to the 1800s when everyone wore beards.
My hair is fly-away fine, thick and not quite straight but not curly enough to be useful. I also have a seemingly permanent center part that persists even though I have not worn it that way for at least 20 years.
I did okay in the 70s when long, center-parted hair was desirable. Haven’t really found a good solution since then.
Mine is fine, straight, and browny-gray. Would work in pretty much any era, but the 50’s “boring white guy” look is best suited to me. It sticks straight out if it’s cut to close, so the crewcut/flattop emphatically does not flatter.
Not true. Some heads - mine, for example - should be well covered with hair.
I had a perm in the 80’s and early 90’s. Made wash-n-go big hair easy. Since then I let it go straight in the 00’s, and now it’s wavy all on its own - I’m pretty sure that’s the new gray texture. Mine’s really fine but there’s a lot of it. I can do any hairstyle. I look better nape-length or longer, though. Right now it’s just past the shoulders. I wear a “classic” shag style (pretty sure it goes back to the 60’s on and off) that can be straightened or worn natural and just needs a little help in the front after I let it air dry.
Always. It’s pretty close to “Jane Seymour as a Bond Girl”, and I really feel like looking like Jane Seymour is never out of style.
(Jane Seymour as Domino. Or, if you prefer, me as classic Black Widow. HAIR, really, is the point here.)
Even in eras where our dominant image is of a lady in a bob or a pixie cut, long hair was still a thing. Mary Pickford wore hers long throughout the '20s – her fans went bonkers when she finally cut it. If I really need to do flapper, I can get it jammed under a hat without much problem.
You learn things doing theater. 
My goatee and long buzz would fit right in with the Beatnik scene.
Oh, I guess late 70s/early 80s. My hair is fairly long, wavy, thinning but coarse. It takes really well to a modified Farrah Faucett flip, and that looks good on me. Most of the time I don’t do much beyond tying it back. I also retain a fondness for juvenile barrettes, pigtails, etc., so that also works for the era.
I also really like a very short cut, almost a buzz (like Mia Farrow in Rosemary’s Baby), but alas, my face is too round now and I would just look very butch. 
Yes, I know this from experience.
