Lot's of other places to look, but I'm unsure what you expect, chukkas are a simple style. :icon_scratch:

$389 -

https://www.herringshoes.co.uk/herring/canterbury_rubber-soled-chukka-boots/brown-suede

$340 -

https://www.bradshawandlloyd.com/sanders-dublin-8533td-dark-brown

 

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.

Lets not forget the original Clarks desert boots, always a classic.

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

 

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.

 

Alden makes a very nice shell Chukka.


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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.

 

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.

 

I second the Paul Evans. They're simple and elegant. I have these in oxblood and just love them.

And have to put in a plug for these Cheaney lined chukkas, which haven't left my feet in 2 months!

 

And have to put in a plug for these Cheaney lined chukkas, which haven't left my feet in 2 months!

Gross.

 

Yes, that definitely sounded better in my head than it does out loud! I still recommend the Cheaney's, but not 24/7. ;-)

 

Sorry I didn't get back here. I got a pair of wingtip boots by Carlos Santos on sale and am happy for now. I'll come back to this thread later this year.

 

I think C&J Brecons https://www.crockettandjones.com/brecon-darkbrown-country-calf/ are the daddies. I've worn mine all winter (and no, not 24/7).

 

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?

 

You wouldn't go wrong with any of these choices.

I agree concerning the L&T chukka. It's a handsome boot but the aesthetic is definitely more casual and rustic than the others.

Concerning a comparison between Cheaney and Loake, I consider contemporary Cheaney having an edge in quality compared to Loake. I have no Loake, but in the past have handled a good deal of it, and the UK made version is most certainly good quality. But I find the hides, and details and solidity of construction on the Cheaney's now being made a bit better. I've now got 3 pairs of Cheaney footwear and it is uniformly beautifully made. The mahogany grained leather I have on two pair is magnificent, with a lovely patina. The pair of Jackie III's have received more complements than any other footwear I own.

The Jackie III's are built on Cheaney's 125 last which has a narrow waist and slightly elongated toe. The appearance is svelte compared to the aesthetic of many boots. The fit is comfortable, but not extra wide as with some English boot lasts. See below -

But I'm afraid the Loake is out of the running for you anyway, unless something has changed. Last I knew, Loake was prohibiting UK retailers from shipping Loake to the U.S.

Carlos Santos makes beautiful, well made footwear that appears to be very fine quality. Their lasts also tend to be among the more svelte, if that is what is desired. And they're a superior value. This boot would be an excellent choice. However, I prefer rubber soles on most of my casual footwear, with the Dainite sole on the Jackie III being suitable for light snow and ice, whereas the CS boot has a leather sole.

 

^^
Were the decision mine to make, I would go for the Cheaney Jackie III, in the mahogany grain option! A very handsome and well made shoe...it's a genuine bargain.

 

The Cheaney chukkas (together with shipping cost) are a little too expensive for my budget. Loake is out of question and even though CS makes very good shoes I don't find them comfortable. That leaves L&T, unless you have other suggestions.

 

I wouldn't give up on Loake - Loake makes shoes for Herring under their brand. I have the Herring Gosforth, which is a Loake 026 last. I'd reach out to Herring and ask for recommendations for Loake substitutes.

 

I'll concur - Cheaney Jackie's are fantastic. I'm wearing mine today (I've been lazy and haven't polished these in a long time.)

IMO the Cheaney's are head and shoulders above the Loake's I have.

 

I'll concur - Cheaney Jackie's are fantastic. I'm wearing mine today (I've been lazy and haven't polished these in a long time.)

IMO the Cheaney's are head and shoulders above the Loake's I have.

View attachment 35451

I think I need these

 

I'm going for Jackie III. I hope they are comfortable too.

 

I got the Jackies but I'm wondering if they're worth that much. They look less refined than CS boots.

 

The price difference largely reflects the difference in labor costs between Portugal and Britain. That is the main reason that Spanish and Portuguese footwear is often such an exceptional value. Beyond that, both are great boots, very well made from quality materials, and you should have what you like best.

A preference for the appearance of one versus the other is entirely subjective, as both are beautifully finished, very handsome chukkas. I have the Jackie III's and prefer them, not because I have them, but because I'm in love with the mahogany grain hide which just keeps looking better, and I prefer the somewhat less radically elongated last of of the Cheaney boot. I also find Cheaney footwear in general, and the 125 last in particular, exceptionally comfortable. I can't comment on the CS boot, as I haven't tried it.

I have no reason to think the CS boot won't be very durable, but I know Cheaney footwear tends to wear well.

Either boot is well worth the price asked for it.

 

^ the difference in price may also have to do with the supply chain.

I don’t have any personal knowledge, but if part of the manufacturing process is off shores and then finished in Spain or Portugal then this, too, could impact the price.