Originally Posted by Douglas
I think this is a bit of a country vs. city thing.
Chelseas can be worn with slim suits and jeans and are perfect for folks in London or NYC.
I think of chukkas as more of a country-style boot, at home with cords and a sweater for a walk through the country but also dressy enough (on the right last) for wool slacks, tie, and jacket.
I'm sort of a country guy myself, so I voted chukka.
+1, except chelseas > chukkas.
IIRC, I own 4 pairs of chelseas and 2 pairs of chukka boots. Though I will say, my chukkas get noticed more often...hmmm....maybe I need to wear the chukka boots more often.