Suz, thank your chiming. The info about heel height with the picture is especially helpful as I have admired your bootie/skirt looks - but I can't do 3 inches.
I don't see women wearing oxfords around Bay St where I work either, I suspect I would if I went for a walk on Queen West. I have found them in a few stores but not the big chains. I tried some "refined" Softino ones, what I call dainty, I really prefer a chunkier shoe to balance my body. I would love to bring multiple pairs home and try out looks but I'm oddly uncomfortable returning footwear - and I wonder if we will have our usual sudden weather change before I manage all that.
unfrumped, I agree dresses and oxfords is probably a young look. I am 39, look it, and am aiming for age-appropriate. In fact I just got a promotion which is why I am trying to get out of my jeans uniform. But I am pretty sure the dark oxfords are not going to be the solution. I just really wanted a flat or low-heel shoe that is warmer/ more supportive than ballet flats, which I don't find super flattering with dresses either. I may have to look for a low, wide wedge heel with closed toe. Sigh. Sounds like a collection of compromises.
I do also appreciate all the pro comments and alternate suggestions too. If I were *in love with* the $200 oxfords I would go for it but I'm not.