I'm currently wearing a kind of leather loafer that has a more almond-tapered toe and replaces a squarish-toed slip-on that I'd still wear from a comfort standpoint but it looks off to me now.
Even in winter there are times I want something other than a boot for going on weekend errands. Also, one of the jeans styles I am wearing in cold weather is better for scrunching than tucking into boots.
This current shoe is not what I would call high style, but it's acceptable for now.
What I've learned is that some version of a leather slip-on flat--but more structured than a typical ballet flat--is a weekend workhorse for me, and so it's a goal to keep updating that type of footwear, whether it's the vamp, the material, the color, the toe shape. It has to be very comfortable, so that sometimes rules out a few trending toe shapes. The "converse" (!) is that I also need a similar lighter shoe--might be canvas or might be light leather--for summer; something that looks good with shorts, as I seldom wear open-toed sandals as first choice.
If I have that type of shoe, I will wear it instead of althletic shoes, and I think it looks better, for me. It can still be difficult to find "the ones," but it helps to know I only need one pair (ideally one pair for each of the 2 seasons as noted) and I'm always hopeful they'll work for more than one year.