I don't know whether to go short or grow my hair out - what would you suggest?

I can't upload photos right now because problems, but I have dark brown shoulder-length hair that's mostly one length with bleached ends that are looking a bit sorry for themselves.

I'm open to going pixie length, but I also want to grow it out long enough to get the underside done a different colour. My hair is fine - although it looks thick - and is a bit wavy. If it goes *too* short, it flicks randomly everywhere and really ticks me off.

I also currently work in catering, if that's another factor that might help.