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You won't go wrong with any of those choices.
Personally I would go with the Chelsea with the Jodphur a close second. I have a pair of Royal Tweed Jodphurs and I find latching the buckle a bit of a pita exercise. It definitely makes putting on a pair of boots a sitting down affair for me.
 

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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.

 

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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.

I very much agree with you on why I don't like chelsea boots (although I would say it was more of a late 60s early 70s thing) and also I would consider some jodhpur boots although I don't own any at present.
 

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Perhaps it's just me or the shape of my leg, but I've never really been able to wear Jodhpurs. I love the way they look, but when I put them on, the uppers flare out too much, pushing out against the material of my slacks. Eventually, they ride up and get caught up at the top of the boot.
 

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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.
That hasn't been my experience.
 

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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.

Wait. What? The 70's? Presumably, my friend, Beatlemania passed you by?
 

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Now you all have my interest. Chukkas I have but jodhpurs? I believe my father had a pair that he never wore. They are attractive . . .

Any reasonably priced recommendations?
 

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Having all three designs on my shoe racks, my preferences are as follows:

*In terms of convenience of use; Chealseas, Chukkas and Jodhours.
*In terms of of versatility of style; Chukkas, Chelseas and Jodhpurs.
* And in terms of frequency of use; Chukkas, Chelseas and Jodhpurs.

Bottom line, all three designs are must haves, but it seems the Jodhpurs see the least amount of wear. :icon_scratch:
 

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I have a pair of J Fitzpatrick Genesee jodhpurs. I really like them but I don't intend to buy any more. I have a couple of pairs of chukkas that I like, but, again, I don't intend to buy any more. I have 3 pairs of chelsea boots and am always on the lookout for more.
 
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