Should I Go Lighter Or Darker? (Hair)

[bagley777]

http://www.flickr.com/photos/bagley777/8293721206/in/photostream

There's a recent picture of me. As you can see, I have medium/dark brown hair, blue eyes, and SUPER pale skin. I'm planning on dying my hair for the first time ever, but I don't know if I should go lighter or darker. Not blonde or black, but a dark or light brown. Either way, I'd include highlights and lowlights so it wouldn't be so flat. :)

Darker: Pros - Might make my eyes pop (I've always thought dark hair/blue eye looked pretty!) Don't have to worry too much about roots, won't damage my hair as much. Cons - Might make me look really flushed (because of my pale skin)
Lighter: Pros - Safer, would make me look "nicer" (I read that somewhere), might go better with my skin. Cons - More high maintenance, Might damage my hair, no "pop" to it.

I'm also looking for style suggestions, I've had this hairstyle for about four-five years now...I'm ready for something new! Bangs, layers? Short, long? What do you think? Thanks!

ADDITIONAL DETAILS: (Don't have to read! Just some things that might be helpful, if you know a lot about this stuff.)
I have an oval face.
I normally wear contacts
My hair is naturally wavy, and I almost never style it.
I have a "cool" skin tone
I'm willing to go a lot shorter...but it needs to be passed the face, at least.
My hair is VERY thick
And another question is anyone knows about colors and skin tones, I was thinking about red-ish highlights in my darkish brown hair. Would that work with a "cool" skin tone?

I just asked like 3 questions :/ Sorry! I'm new, and curious. If you can answer any one, it would be much appreciated. :)

[factor-fiction]

I like your Grand Canyon pics that are on there.

I'm no expert but for what it's worth I think your hair colour looks fine as it is.

[Charity]

Me too! You're lovely just the way you are :0)

[rockyracoon]

Whilst you do look lovely as you are, I understand the need to change your hair. Between my teens to mid twenties, I was every colour under the sun, no matter how I may have liked it, I always migrated back to my natural colour (which is similar to yours), maybe with a bit if red or chocolate tones but always the same colour, no roots and you know it has to suit you. You have quite dark eyebrows so don't go too light, but you are young and you should have fun with your hair, and I go by the fact that i'll grow back. Book an appointment with a GOOD hairdresser. Good luck, post a pic u of the new you after you've done it.

[mrs_overall]

My advice would be DON'T change your hair colour as it suits you perfectly as it is.
Once you start using dye you can never stop and it will make your hair feel like straw.
There are loads of magazines you can look at to help you chose a new style or ask the advice of a good hairdresser and your friends.

[sandyRoe]

Your hair looks ok.

http://www.youtube.com/watch?v=5VQtc2Ajkj4

[cazzz1975]

whilst lighter hair would look nice, it is a REAL commitment, especially if you are naturally a brunette, its not simply a case of buying a box of hair colourant every six weeks, light hair on a natural brunette needs almost weekly/fortnightly attention, normally from a hair dresser as they can be sure to cover everywhere.

[maggiebee]

Your hair, eyes and skin colour match perfectly, why change one of them?

[tamborine]

A few veil blonde hilites in front would accentuate your eyes. An 'A' front-shape would enhance your cheek bones and layers would give your hair more structure. This would be minimum hilites, lightly spread and wouldn't need frequent re-tinting.

This:

http://www.sheknows.com/beauty-and-style/hairstyle-photo-gallery/long-hairstyles/rachel-bilson-2

[Hopkirk]

Keep your natural look

[islasmum]

I've found it quite helpful in the past to go on to some of the Virtual Hairdressers online, where you can upload a photo of yourself, and try out various different lengths and colours before you commit yourself to anything. Having said that, if I had hair like yours, I would leave it as it was, because I think it looks really nice, but I understand why you would like a change. Best of luck whatever you decide.

[boxtops]

Your colour is great, same as mine - don't be tempted to mess with it. All I ever do it get a hairdresser to put some red/copper streaks in for the festive season (and I haven't done it this year). Go to a good salon and ask for their advice, based on your facial shape, your hair quality, your lifestyle.

[shoota]

Google - 'Catherine Zeta Jones Chicago' for my suggestion.

[shoota]

http://www.allure.com/celebrity-trends/2010/movie_hair_ideas_and_makeup_looks

[karenmac60]

I won't tell you not to change cos if you really want to, you will. But from someone who has very pale skin and eyes and has had every colour of hair imaginable, going lighter may leave you looking washed out. I know I just looked ill when I went blonde, plus it takes a lot of maintaining unless you are happy to have several inches of black roots showing. I always end up going back to red cos it suits me best. If you feel the need to try a few different colours till you find something you think suits you then go for it - but be prepared to lose the condition of your hair and spend a fortune on lotions and potions to make it look and feel healthier.

[bagley777]

Wow, thank you for all of your advice! I wasn't sure if I would get any replies at all. You guys are awesome! :) And thank you again for the compliments! You've talked me out of it, I think I'll just put some high/low lights in my hair. Still undecided on the style, but the one tamborine suggested is very cute. I wish I could chose multiple best answers! Thanks again, all of you. Every single person helped. :)