Laughing at PPs speaking with such authority on what is 'dated' - knee high boots are on trend right now, as are pointed toes. Also those are more kitten heels than stiletto. With a midi dress like that knee high boots can look better as it lengthens the leg.
OP if you really hate those boots it's styled with then yes, tights and chunky (flat!) ankle boots would work. I would go sheer tights over opaques to minimise mumsiness (no shade on opaques, it just depends on the outfit).