The City and the Work handles are the same (at least mine are). Both fit the same under your shoulder. There was a thread earlier about the 07 works having longer handles I believe so I suppose it depends on what year your Work is.
welp, i've got 3 works & i love all of them to bits ...one thing i can tell you is the handles stretch out quite a bit with use...but i still can't get them over my big winter puffer coats!!!
i can fit my work over my winter down jacket (my jacket is not that puffy tho) but it usually slides down after a little while so i have to re-adjust it.