Hair help!

Alright ladies... slightly long post. I need some hair advice! I'm making an appointment soon and can't decide what to do.

**I have been keeping my hair relatively short because I used henna dye for years but got tired of the commitment and dyeing my hair myself. With henna you HAVE TO let it grow out completely before using standard chemical dyes. So that is the end goal and I'm super close!**

Here is my hair now:

There is literally nothing I like about it. It's awful lol. I found a new stylist who is amazing with short cuts so I feel confident taking some major length off. I can't decide if I want to keep a little length or just go balls to the wall and get a shaggy pixie.

Here's a picture of me with short hair in high school:

Aaaand some inspiration pictures...

Longer:

Shorter:

Please vote and let me know what you think. :)

Posting in this group as well because my other poll is neck in neck!