You all are so sweet! Thank you for the kind words, ladies!
I know I've worn a few "on-trend" looks and found myself disliking them. I think deep down, I still bat for Team Dressy (with a hard edge). It's hard finding comfortable dressy shoes that aren't super casual (like sneakers - even when I purchase unusual fabrications) or too classic. I really miss my heeled edgy shoes and how it just adds that extra "oomph" to an outfit. I haven't found any of those cut out booties that suit my tastes and comfort requirement, otherwise they would be an option for me.
@quietgirl: I'm glad the on-trend casual sneaker look works for you! I've seen it worn here in YLF and everyone looks amazing. I can't seem to "own" the style because it just doesn't feel like "me" I guess the search for the perfect shoes continue!
@Dee: yup - obviously I'm not used to this very casual look! And if it wasn't for my arthritis diagnosis, I wouldn't be thinking about shifting styles. I already had a lot of elements in my style worked out, but seeking comfort for the peaks of my health was an absolute game changer. I think if I dressed classic or a bit more on the casual side, this would've worked out. Even my relaxed looks are quite dressy!
Carter has recommended the Anne Klein Sport brand. I tried on a wedge and it was nice and sturdy (still too high of a dip though). I'll be looking into their flats.
@Shannon: Yup. I was well known in all my workplaces for my shoes. I always had some sort of edgy/funky heel that just elevated the outfit. With all the slouchy, oversized dolman/kimono tops I've been wearing, the right edgy heel would've given it that polish.