While I have trouble gettiing a good fit and proportion in skinny or tapered pants as a general rule, I have acquired a few slightly fitted/tapered pair that work in my wardrobe and work well with longer or oversized tops, for a change of silhouette. The biggest thing to watch out for is that this type of pant can veer into ice-cream-cone-like.
I also have a couple of pairs of flats with slightly pointy toes, that "go" with said pants.
However, I've noticed that when I match up the skinny pants with the pointy flats, the resulting look is not exactly what I want. It's almost too prim or prissy or something. Whereas, if I wear a shoe with a bit more substance--not clunky but maybe a refined oxford or a typical loafer--I may like that better. I think it is not just vamp height but more shoe overall. It could also be heel height, as the loafer or oxford may have a 1/2 or 3/4 " heel, but seems to be true even in a flatter shoe.
I was wondering if that is due to a real rule of proportion ( in current style culture, of course) --that the amount of shoe "presence" balances the taper the way a slight bootcut pant balances the pear shape., or if it's just a personal preference. Usually I'm trying to up the ladylike aspects for work because some elements of that are anti-frump and sometimes less casualized. I can see how the more tapered shoe helps me with more straight or trouser styles, but I did not expect it to work in the wrong direction for tapered pants.
What do you think? Have you had similar reactions?