My $.02 (and that's about all it's worth):
Chukkas? Yes, love 'em! Chelseas? Yes, but I've never owned any. Jodpurs, maybe. Others, perhaps, but probably not. I know that some of the shoe mavens of these fora do like ankle-high lace-ups with "dress shoe" styling and construction, but they're not my taste. Such footgear impressed me as "retro" and "old-mannish" back when I first began to take an interest in such matters about 50 years ago, and I've never seen fit to change my opinion in the passage of a half-century.
Ankle-high laceup boots are fine in the role of outdoor boots or work boots, of course.