Originally Posted by JLibourel
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.
Just to show that "consistency is the hobgoblin of little minds" (Wasn't it Emerson who said that?), within two days of my original post, specifically, "Others, perhaps, but probably not," I just ordered the discontinued Allen-Edmonds York boot in brown--a zipper dress boot with what looks like a 7-inch upper to judge from my old catalogs. Partly, I just thought it would be something different from the bals and bluchers I usually wear. Mostly, though, it was because I could get them at thieves' price from the outlet--$109. (They retailed for $315 when most A-E dress shoes went for $285.)