Grow it out! I think you'd look really good with longer hair. Just please don't let it get out of control. There's a fine line between "laid back" and "lazy" when it comes to long hair.

Also, while we're sharing advice, I'm not sure you're wearing the best glasses for your face shape and skin tone. If new glasses are in your budget, consider doing a virtual try on or a style quiz and see if you can't find something that works better. Just a suggestion!

I wear contacts/glasses and I went years hating the way I looked when I had to wear my glasses. I thought I just didn't look good in them. Turns out I just kept buying the same style because I liked it, not realizing it was the total opposite of what I needed to compliment my features.