My only real problem with this outfit is the back. The front has cute (and I believe, period-appropriate?) pleats on it, but the back just looks cheap by comparison. I, too, wish she came with button boots instead of the boring mary janes, but they're decent all-purpose shoes, and they blend in with the tights so that's cool.
I have the Mattel version (I got my Sam in December of 2008), and the fabric is really thin and kind of wimpy-feeling.
Overall, I'd say B.
My girls: PM Felicity, PM Kirsten, Samantha, Rebecca, PM Molly, Jess, Mara (#8), Shannon (#15), Marjorie (#20), Margie (#21), Dawn (#27)