LisaP, you totally get it. Yes, I hate winter right about now, too. I was going to replace my Aquatalia motos this year, too, but alas, a similar pair did not appear at NAS (or elsewhere in my price range) so I had my old ones reheeled, which seemed cost effective but actually created a problem. The cobbler put a NON-lug heel on a boot that has a lug sole front and now I slide more in them than I used to. This slipping and sliding is a big deal -- I've already fallen once this year and almost fell a couple more times. I cannot afford to break a bone -- and so yes, this is another reason my hard-soled dressier booties are not wearable.
Janet, I think you are right. I need to break down and admit to myself that my environment and my lifestyle are not hospitable to my winter style and stop buying items I can't often wear. Like dressier booties. In theory they are great but in practice, they don't get much wear. Of course I need a pair or two in my closet, but not the um...nine pair that I currently own. I should have four booties, and nine pair of snow-worthy boots! I mean, considering we get snow/ rain/ slush/ sleet from December to mid-April, that makes sense. Well...onwards. Lessons learned. By the way, I wish Sorels and Flys fit me better -- I like those boots. I may try something like that anyway because different styles can work even by a maker that doesn't usually. The heel or wedge makes them feel a bit more stylish.
Tex, thank you. I am also attracted by those hi-top Eccos (but not for winter wear here, alas). I love my white Ecco Softs so much, and got them largely thanks to you, Gaylene (who sourced them for me), Smittie, and Angie's recommendation. I think you are right that the trick is looking for slightly less stompy or rugged looking styles that still have the function....
Emily, I ADORE those Cole Haans. Gorgeous. I actually love refined Chelsea boots and would have zero problem wearing those -- except that I need something warmer and more rugged for the conditions, I think. We walk a similar amount. Walking pretty much saves my sanity and I love it.
Khris -- Where I live, shopping and errands means walking downtown. I do also "go for walks" as exercise, but for that I am okay wearing gear-type footwear. And mostly my walking is part of my day's routine. Not a mall in sight. I go to a mall maybe once every two or three months at most, and usually when I am travelling, at that. Meeting friends, I would walk to the destination and then if it were a restaurant (say) there wouldn't really be any place to leave my outdoor footwear. (As you can probably imagine, mats are often used over top of carpeting and wood floors in winter here.)
Sisi, I might try that -- go for some juxtaposition. Sigh.