I struggle w pants + shoes every winter! When I can wear sandals or boots it's easy- tall boots w skinny pants, booties under wide pants. I only wear almond or pointy toes. Flattering is more important to me than trends.
Transitional shoes though are challenging, and not just due to fitting them on my duck feet :p
Mules/slingbacks can work w my feet, but I step on the back of my pants.
I have loafers, but they felt way too classic. Ok maybe to elevate jeans, but with trousers I felt normcore and older.
Ballet flats feel too Ingenue, especially with skirts. Pumps feel too bombshelly with skinnies. Sneakers, I just can't outside the gym.
I bought sandal booties, which will be my transitional shoes. To me they're 50-60 degrees shoes, not real summer shoes. I remember them working well for me before, but will report back in November when it's cold enough to wear them!