Styling Short Bobs

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Thanks for the advice. I don't mind blowdrying at all! It doesn't take as long to dry my hair as it used to. I have a round brush but have difficulty trying to flip my hair out with it.

I'm also wondering how I can do a "messy" look. Funny how the bob looks so neat on my head (regardless how I mess it up), but it was the "messy" look that I really liked when I had long hair. Anyway that can be achieved?

You can make baby ponytails or braids at the sides.  I used to do that with a bob.  Really, you could do as many braids as you like. . . if you put some small ones all the way around, it could be nice, I think.  Sometimes I would put beads on the braids, and that could be kinda Egyptian-cool if you put the braids all around, with little beads on them.  I also used to paint streaks in my hair with markers, back then, but that might not show up for you, if your hair is very dark.  If there's a bit more opaque gel or hair mascara or something that works, you could streak with that, though.

If you need to look formal, you could put it half-up, and maybe tuck in a flower, or use a decorative clip to hold it.  Or maybe twist it back, pinning it along the way, and tucking under or sorta bunning the ends once you reach the back.  To make it look more formal you could use jewelled hairpins for the pinning-back, or tuck tiny flowers or baby's breath in here and there.  If your hair will hold a curl, you can do something Marilyn-esque with it, and that would look glam without any ornamentation.