buy an insert. they sell cheap gel ones at the grocery store (like dr scholls). there’s also fancy ones that help with feet issues like plantar fasciitis. if you wear heels a lot, and the bottoms of your feet are suddenly hurting a lot now when you walk, you might have plantar fasciitis. if that’s the case, you’ll need to take a break from heels, and wear some cushioned shoes for a few months so your feet can heal.

comfortable boots. depends on the weather. muddy ones, you would need tall rain boots. hot ones, just short ankle boots.