Okay, a guy buying a purse for his wife may strike many as completely foolish.  But my wife had a tendency to buy a purse from some bargain bin, hate it, try to use it, then replace it or return it, meaning that she was buying 3-4 purses a year and hating all of them.  I kept suggesting she just pay the extra to get a decent purse she likes, but she's Scottish, so....

A friend told me about a purse that he bought for his wife (she told him the make, size, and color).  So I checked it out and bought my wife a similar one -- the red leather version of this.

She used it for three years.  She still could be using it, but it was getting a little worse for wear, so I got her this model.

She says this microfiber one is lighter than the leather one and, of course, black goes with everything.  Seems like a very tough microfiber, so I imagine it will last just as long.  She loves the weight of it on her shoulder, the pockets and clips and means for organizing all the stuff she carries and can always find her stuff.

Shoot small.  I originally got my wife the Medium one, but it was way too large (she's 5'2").  I'd guess the Extra Small would be for people up to 5'5" or so.