Love them on you.
My flares definitely end up migrating lower on my body over the course of a day, so my PPL becomes a bit hem-dragging by the end of the day. I don't find length shrinks if I don't machine-dry. So I think you'll be ok lengthwise.
I got a pair of (gasp) high-waisted black flared jeans from Anthro, but they have that strong dye smell which I am going to try to banish before committing to keeping them. The fit is amazing so I hope I can kill the smell. And I know I look awful in high rise if I tuck a top, but I think I can pair them with tops that don't need to be tucked.