What footwear with dresses this autumn

[afalmartin]

I'm a teacher and wear lots of dresses for work, tend to wear similar ones for summer and autumn just swapping wedges or court shoes for boots and tights but not sure if boots are a bit passé? (Or are they classic? What length? Heel or style is best to avoid looking like an outdated frump?

Boots are boots. They are only frump in the eyes of people with nothing better to worry about.

I have:
Knee-length flat boots
Knee-length mid-height boots
Flat ankle boots with buckles
Flant ankle boot-brogue looking things
Blue suede ankle boots with laces
Cherry red DMs that are 26yo.

I don't have biker boots, cowboy boots or Converse.

As long as they keep your feet dry and warm and you are confident wearing them = win!