WIWIW: Hair

I've done a couple of WIWIW (What I *wish* I Wore) posts in response to blogland's versions called What I Wore Wednesday. Feel free to read them here, here, and here. I ain't got nothing in my closet you'd want to see, trust me. In fact, my jeans are so threadbare and worn that I've split 2 pairs of pants in 2 weeks. If that doesn't make you want to lose some weight and get fit, I don't know what will!

My clever friend assured me that all threadbare pants split like that so I am choosing to believe her. I DID realize that one pair of those jeans was purchased 8 years ago from Goodwill for $3. Maybe it was time for them to go in like 2005?

Back to the point: WIWIW. This week I've been thinking a lot about hair. I've cut my hair before and always regretted it, except for the one time I chose to chop it off for charity. When I donated my ponytail to make wigs, it felt so purposeful. 

Very opposite to purposeful was the time I cut my hair to an Annie-style 'do because my grandfather gave me $100 to do it. True story. I've shredded all those pics but this will give you a good idea of what I looked like:

*Shudder*

The good feeling from donating hair also helps when all the awkward-hair-stage annoyances crop up as I'm growing it back out {which I ALWAYS want to do as soon as I cut it!} This time around, I wanted to give to a charity that makes wigs specifically for kids. So, we'll see if I bite the bullet and go for it.

I've been thinking/dreaming a lot about changing up my hair pretty drastically. Many of the organizations want minimally processed hair without coloring or highlights. Because of this, I wonder if now's the time to go ahead and ponytail it/chop it/donate it and THEN proceed to color it and experiment. What color would I go for, you ask? I've always been drawn to red hair {must be my Irish roots!} and I love how this gal Katie styles/colors her hair. 

Her blog is called Skunkboy Blog and she also makes adorable handmade critters. Awww.

I've toyed around with the idea of going really dark {maybe it's my Native American roots!} or edging more toward my natural tendency for blonde highlights if I spent more time in the sun. My hair typically looks like these pics in that perfect world of sun and no responsibilities (read: when I was 13):

I also like some version of those blonder looks but with the ombre style that allows for darker roots (a subtle, natural dye job though). Something like this:

Just kidding. Nast. I mean, like this:

 Or this:

 Not so much this:

I guess if my hair is chopped, I can't pull off these longer ombre styles as well. I may have to wait for that until it grows out a bit. 

Any ideas on what might look good on me? Should I go for it?