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Personally I am more of a fan of suede chukkas.
Thursday Boot Co. suede chukka in cognac suede. I have this shoes and like it quite a bit I think it is a very versatile shoe that can be quite causal.
Footwear Brown Shoe Beige Hide


Lets not forget the original Clarks desert boots, always a classic.
Footwear Brown Shoe Beige Outdoor shoe


If plain chukkas are not your thing they can come interesting colors like blue or with broguing.
 

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I have a pair of Loake Pimlico chukkas in dark brown suede that I like very much. Got them on Massdrop for a significant discount over MSRP (never mind that Loake now doesn't let retailers sell to the USA).
Herring sells a variety of Loake shoes, including chukkas, rebranded as Herring shoes, and will ship them to the US. I think the Herring Gosforth is a Loake Pimlico.
 

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OO, as to the OP, what do you want to wear these chukkas with? Need to know that.

My personal favorites for dressier Chukkas are Paul Evans, which sometimes go on sale got much less than their usual price, and Loake.

For casual, my new favorites are the Astor Greenflex, due to the awesome quality/feel of the suede and how well the last fits me.

For casual where I may bang them up, my trusty AE Bellvues are great. They're nowhere near as sleek as the PEs or Loakes, but the leather used is super thick and durable, and their overall profile is not unattractive. As a bonus, AE seems to not give much love to this model, and you can regularly find them on clearance or shoe bank. I paid like $120 for mine. Due to the durability of these (man have I beat mine up, and they still look fine), if you want a more casual pair, these are deserving of being in your decision matrix.

I have a pair of Thursday chukkas, but the shape just seems off to me. Not my favorites.
 

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Does RM Williams still offer their kangaroo hide laced Craftsman (Chukka) design. If so they are quite the comfortable and very handsome shoe. Hence the pair that sits on my shoe racks between wearings! As I recall, they price out at less than $400. ;)
 

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Herring sells a variety of Loake shoes, including chukkas, rebranded as Herring shoes, and will ship them to the US. I think the Herring Gosforth is a Loake Pimlico.
I just bought a pair of Herring's Gosforth II chukkas. I like them. I thought they were their version of Loake's Kempton, as both are made on the 026 last (Pimlico is made on the Capital last). Either way, if you like Loakes, just buy Herring's version. I wasn't disappointed.

Sent from my iPhone using Tapatalk
 

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Herring sells a variety of Loake shoes, including chukkas, rebranded as Herring shoes, and will ship them to the US. I think the Herring Gosforth is a Loake Pimlico.
Herring Gosforth is a Loake Kempton on the 026 last.

I have the Gosforth in now discontinued burgundy.
Even nicer though are my Cheaney Jackie chukkas.
Very comfortable from the first time I put them on.

Mine look just like these, though this colour may be discontinued now.

 

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Herring Gosforth is a Loake Kempton on the 026 last.

I have the Gosforth in now discontinued burgundy.
Even nicer though are my Cheaney Jackie chukkas.
Very comfortable from the first time I put them on.

Mine look just like these, though this colour may be discontinued now.

Interesting! I'm assuming the boots above are the Cheaneys. I purchased a pair of Jackie III's from Herring this past autumn, and they are as depicted below, and made on Cheaney's 125 last. It appears my chukka is on a different last that's been "updated." But the color which they describe as mahogany is quite similar to yours.

Irrespective of the different last, mine too are very comfortable, and among the most comfortable footwear I own.

 

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Interesting! I'm assuming the boots above are the Cheaneys. I purchased a pair of Jackie III's from Herring this past autumn, and they are as depicted below, and made on Cheaney's 125 last. It appears my chukka is on a different last that's been "updated." But the color which they describe as mahogany is quite similar to yours.

Irrespective of the different last, mine too are very comfortable, and among the most comfortable footwear I own.

Sadly, my Gosforths fit ok, but are a tad bit too narrow in the toe. Absolutely fine for a bornalday and I wouldn't notice, but I wouldn't want to wear them on a day where I'm out and about all day.
 

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Discussion Starter · #19 ·
I'm back in market for a pair of chukkas. The contenders are

Cheaney for $359 https://www.herringshoes.co.uk/cheaney/jackie-iii-rubber_rubber-soled-chukka-boots/dark-leaf-calf

CS for $292 https://www.herringshoes.co.uk/carlos-santos/7991_chukka-boots/braga

Loake for $215 https://www.herringshoes.co.uk/loake/pimlico_rubber-soled-chukka-boots/dark-brown-calf

and L&T for $341 https://www.skoaktiebolaget.com/collections/boots/products/lof-tung-cole-utah

I'd get the L&Ts in an instant if it wasn't for the protruding soles. I don't know much about Cheaney or Loake. Are they comfortable?
 
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