Chukka vs Chelsea vs Jodhpur Casual Boots

I would also select the chukka.

I don't really care for the looks of Chelsea boots, in no small measure because for me they will always remain associated with '70's fashion, which I dislike.

I've always been fascinated with Jodhpur boots and had been thinking of adding a pair to my rotation. While I had previously read an opinion that they should be confined to equestrian wear, I'd find them very suitable for any dressier casual wear.

But I recently read a remark by a wearer that has made me rethink my interest. Specifically they said to effect that they look better off than on, and they found that the normal break at the vamp below the instep caused the upper to bow outward and affected fit as well as appearance, unlike a chukka which is laced over the instep.

I have no experience as to the validity of that report, but have no reason to doubt it either. So for that reason alone I would hesitate to recommend them.

My most recent addition has been a pair of Cheaney chukkas (Below.) and I've been very pleased with all aspects of them.