I’m 28, and I’ve been doing the same thing the past few months with dark blue. It’s fun! Go ahead and dye your hair, and if anyone gives you any guff for it, point out all the shallow things they do to make themselves feel more attractive. 
I’ve had graying hair since I was in high school, it looks light brown for a distance but when you get up close you can see gray peppered in. Chicks (on the rare occasion that I get that intimate) really dig it. “Oh, your hair is all silvery! Woo!”
Embrace the gray, and spend the time you’d expend worrying about and fiddling with your hair on other areas of your life that will make you happier and more successful.
Stranger
Problem is the OP sounds like he is still in the in-between stage. If he was all or significantly grey he could go for that “silver haired fox” look of Clooney, Cooper or Martin. If it was a distinctive pattern, he could even go for that Mr Fantastic/Reed Richards look or how some people have a “skunk stripe” that just sort of goes grey first.
Unfortunately, a handfull random grey hairs scattered around your head just look like shit. It just looks like you should do something to fix it but just can’t be bothered.
It’s sort of like going bald. Once you reach that critical mass of baldness, give it up and just shave that head. Combovers, ponytails, and other half-measures just draw attention to it and make you look older.
Quotingthe very wise Michael Ventura:
Don’t dye your hair unless you’re a woman over 40 and you dye it the color of my obsessions. Even then, don’t cover up all your gray. Gray is gorgeous. And if you’re a man, then really don’t dye to cover gray. Dig it: EVERYBODY KNOWS. And they talk about it in a snide way behind your back. I’m not kidding.
I must tailor my answer to the specific person who asks it (though I’m leaning towards no for all of the excellent reasons given already), so I’ll wait in hopes of a picture.
I’m 55 and have a mixture of black and grey hair on my head, moustache and beard.
This doesn’t bother me, but if you want to dye, go ahead.
Or you could buy T-shirts which say things like:
- my hair is grey because my energy is in my groin
- would you like to check to see what colour hair I have elsewhere?
- my hair is grey but my equipment is superb
- I have the hair of a 42 year old, but the body of an 18 year old
38-year-old female ringing in here.
I’ve been dyeing my hair since 1984. I started finding grey hairs in 1996. I’m only bothered by the amount of grey showing up in the last year or so.
Grey hair does not dye well. Temporary colors will not work at all, and if the brown is too light, it will not cover your grey, just make the rest of the brown a shade or two lighter than it is normally.
You have a couple of options. If you dye yourself, use a color that’s as close to your natural color as possible. If you’re medium brown or lighter, the greys may not “take”. If you’re usually a darker brown, then you should be fine.
For your first time coloring, I’d really recommend going to a salon. The colorist should tell you what color to get from a store to match what she/he used at the salon. When you do try coloring yourself, do it at night with no other plans, and with a free morning the next day. If you really mess up or hate it, you can wear a hat and run to the salon the next morning to get it fixed.
Another option is to get highlights. Some caramel highlighting will mask the greys without having an overall “dyed” look, but that method is definitely best maintained with a colorist, you’ll have to do it about every 6 weeks. The upside of that is it takes less time than dyeing, and is easy to maintain from the perspective of just having a standing appointment to keep, and takes less time than for you to do it yourself.
I have two uncles who are in their late 50’s, and their completely single-toned dark brown hair looks over done at their age. Men, much more than women, need to know when to let the greys just be natural, because at a certain age it just looks like a wig or a toupee. Silly.
On the other hand, I’ve been very happy with the results I get from henna. It’s translucent, so you don’t end up with a flat, artificial-looking single-tone color. My greys pick up the color very well. It also conditions your hair, and chemical dyes tend to dry out or otherwise damage hair, sooner or later.
You can get a dark brown with a combination of henna and indigo (PDF).It’s time intensive to the extent that you need to leave it in your hair for a couple hours, but with short hair (I’m assuming you have short hair) getting it into your hair would take maybe 10 minutes. It probably wouldn’t work out to that much longer than doing it at a salon, if you include travel time. I use less henna than they recommend for my hair length, and it still works out fine – so rather than $60 (plus tip) every six weeks at a salon, I’m spending $40 for enough henna to last me 6 or 7 months, doing it roughly monthly, for hair that’s about 3-4 inches past my shoulders. For short hair it would last way longer.
All of which is to say – dye it if you want to. It doesn’t matter what anyone else thinks, you need to be happy with the way you look.
Been going grey since I was 18 but it’s been a slow process, at 34 I now have two heavy “badger” stripes. One down each side of my head, I’m told it looks good and I like it so what the heck…leave it as it is
I’m a 27-year-old female, my hair has started to go gray, and damned if I’m going to dye it! When I see women with long grey or white hair, I think, “How elegant and self-confident!”
My hair is graying in a patch at the top left of my hairline, so I’m hoping for a cool stripe. 
If you want to dye your hair, then yes.
Whether you should, depends on what change you will think it will make in your life.
If you are doing it to attract more women who are close to your age or younger, then it will probably work since you will probably look younger with your darker hair.
definitely try doing a different cut first - to see if the grays are noticeable because of how you have it cut. A cut is much easier to maintain than a color.
But color if you want, if nothing else to say you tried it instead of just wondering if you should . . .
Everyone is obviously agreeing: it’s your call on what you do.
That said. . . I vote NO. I was in the same boat: male, started going gray in college, by the time I was 28 I had a lot of it. I’m 34 now and I have probably 75% silver, 25% dark brown.
I always wondered along the way whether I should dye it, but I never did, and now I’m thankful that I didn’t.
Assuming that your gray is coming in evenly (i.e. flecking in, no patches or skunk stripes), in a few years it’s going to look really good.
Benefits:
– Looking older when everyone else looks younger. Gray hair in your forties & fifties may be a bad deal, but in your 20s, it makes everyone around you-- your boss, your co-workers, sexier older women-- think you’re wise beyond your years. Totally superficial, of course, but in my career and dating life, I never once found it to be an impediment, but usually the opposite.
– No maintenance beyond your normal routine.
– No snickering behind your back: people may remark about you being gray earlier than normal, but nobody likes a man with a dye job. It reeks of vanity, and vanity in men is a no-no.
– It beats THE HELL out of going bald. Which is, in fact, my stock witty retort when anyone ever asks me if the gray hair bothers me.
Now, IMHO the one and only downside to having gray hair is that younger women don’t find it as sexy. So, if you’re looking to date nubile 22-year-olds just off the quad, expect the gray hair to hurt your chances.
That said, women your age or older will, on average, find it distinguished, and even sexy. YMMV, but that’s been my experience.
As a woman the OP’s age, I agree with this. Most men look find with some gray, and quite a lot of them look hotter than they did before.
If it’s really bothering you, there’s no harm in coloring it. If you decide the gray is better, it’ll still be there underneath.
I think this is less true than it used to be. When I was in college, I frequently ended up in the middle of conversations about how ridiculous it was that women were “expected” to remove body hair (legs, pits, etc.), and men by and large weren’t (even beard shaving was optional, and frequently used as a decorative accessory much like women’s head hair was).
A few years later, it’s now commonplace for men to shave/wax their chest hair, pit hair, and bits. Even non-“metrosexual” men do it. It more or less evens out with women, now. So aside from the fact that other people’s expectations are less relevant than your own, expectations have changed in the last several years.
Plus if you pick lighter/translucent dyes, I doubt most people will notice, short of those who’ve seen the “before” and “after.” If you pick a flat, single-tone color it’ll look a bit off, since no one naturally has a head of hair where every strand is exactly the same color.
(Also, people tend to see what they expect to see. I was once stopped in the street to be asked if I’d like to be a hair model. I was going through chemo and wearing a wig at the time.)
This is true, which means you can always try it, decide you don’t like it, and change your mind. Assuming you keep your hair short like most men, growing it out wouldn’t take that long. Or you can try a wash-out dye first, which will be gone after about two weeks’ worth of showers.