I would probably go with the 2" heel. But of course "it depends." It depends on what hole in my closet the shoe fulfills. Is it a go-with-anything color? Do I already own something similar? Is the style more of a work shoe, dress up shoe, city walking shoe (all those cobblestones - flats are best)? What is the pants length I plan to wear with them?
I say I'd probably go with the 2" heel just because I'm in need of pumps at the moment, having gone on a long streak building up my flats collection. I also do like the extra leg-lengthening effect of a heel. Except with clamdiggers or cropped leggings; for some reason, I think heels worn with these make my legs look too spindly. I'm not sure why that is! I have no problem wearing heels with skirts that hit at the very same length. My eye just can't get used to the look, I guess.
Of course if we are talking winter shoes, then there's the added concern of needing a shoe that can be worn on ice. If it was a wedge, it might work. I guess I'm saying the "it depends" includes - what is the shape of the heel?
Nordie's has a version of my favorite Me-Too flats in a 2-inch wedge (I think others here also have them), I tried them on and they looked funny on me- made my feet look clunky. I'm not sure why that is.
