No experience with the Medela bra but I have the Simple Wishes and I'm a huge fan. I have large breasts and it doesn't fit perfectly (some overhang on the bottom) but it holds onto the breasts in circumference very well. I use it every time I pump, which is every 2 hours and it does the job perfectly. From what I heard it is the best choice of the 2 and I would recommend it.
Re: handsfree pump bra simple wishes or medela