Its a pub night out. Im 52. I'll be wearing black skinny jeans. I usually wear ankle boots with block heal for casual winter. But lately I've been wearing light weight white canvas flats no socks. Jeans are ankle tapered. But these shoes look odd in winter as they are more summary and are looking a bit battered. Don't do kitten hills. What else could I wear that is not a boot or open toe ? Don't do Ugg.