Want to wear whichever socks you wish with chukka (or higher) boots but still have look and warmth of kilt hose?

Try leg warmers.

My calves are “normal” (c. 16”) for my height and weight (6’, 195 lb.).
Even “one size fits most” woman’s (!) leg warmers fit comfortably.

Downside: acrylic or acrylic fleece or wool-blend more common than wool.
Upside: No toes or heels to wear out.

Example:
http://www.vermontcountrystore.com/S...armers&x=0&y=0