I'm working on developing an outfit formula for evenings out (date night, girls' night, etc).

My city and social milieu are very casual but nevertheless I'd like to get gussied up a *little* bit when I go out.

So I'm thinking about jeans + silky tank or camisole + fuzzy cardi or slouchy pullover for a cold-season formula. See finds (which are not anything I own, just grabbed things others had collected to give a visual).

I like this formula because the combo of bare camisole and soft sweater feels -- dare I say -- sexy to me. Plus I need to be WARM, and want something a bit fluid because I like to enjoy going out to eat you know?

Where I'm stumped is footwear.
-Tall boots feel too everyday.
-I don't fancy the rolled jeans-and-ankle boots look plus I find it impractical (too cold) so that's out
-ballet flats seem weird juxtaposed with my winter coat -- too insubstantial
-High/stiletto heels don't appeal to me. Not practical/comfortable and not a good fit for my style. Would like to keep heels at 2" or under

So...what then?

A fancy (velvet/brocade/embellished) loafer?

Something...edgy? Overall, my style is not edgy. But sometimes when dressing to go out I want to wear some of my vintage costume jewelry -- and it often feels too prim, too staid combined with dressier clothes. Like I'm playing it too straight. (Works much better juxtaposed with truly casual clothes the way I've worn it during the holiday season.) So I find myself pondering an edgy element. I just don't quite know what it would be. Straight up moto boots/jacket aren't quite it.

Anyway, anyone have any ideas, now that I've explicitly excluded basically every category of footwear?

Hit me up with your musings, links, finds -- I'm in total brainstorming mode here.