There is a new soft duffle that my mom is dying over. It comes in leather and signature and it is under $300. It has a long strap that you can wear shorter too. It is a very classy bag and looks good on my mom. It is the shorter version of the duffle and it is online right now. Check it out.
Legacy is very nice but my mom doesn't like any of those because they are not comfortable to wear for her.
I know that it isn't always the easiest to please moms. I have purchased three bags for her and returned all three. We tried the Legacy Shoulder Zip (too small and too short for her), the signature stripe camera bag (too small and a little akward looking for everyday), and then the meium Carly (didn't like the inset zipper). Yup, she is a picky one. She loves her Chelsea bag so I bought her another of those last week on sale.
Good luck!!!