I never used to be a chukka lover, seeing them as too casual for formal outfits and too dressy for casual ones.
Converted by the versatility of a pair of suede chukkas made by Crockett & Jones for Foster & Son, my mind was changed - since then I've always had a couple of chukka boots to hand / foot. This review will cover the four chukkas currently in my rotation - since the pricing ranges from mid (£395) to pretty much the highest RTW available (£1,120) it's also a chance to look at the improvements in finishing and materials as you head up the price bands.
In an ideal world, I'd have some Clark's Desert Boots to compare to as well - I'm not a huge fan of the brand, but they are the quintessential Desert Boot (at least on r/malefashionadvice and r/goodyearwelt). But this isn't an ideal world, so... here we are. Four boots. Take it or leave it.
Tricker's Polo Boots - Leather, UK 9.5, £395 RRP. A light brown calf leather, very pliable, and unlined which adds a lot of flexibility. Arguably a bit too much pliability, as the leather pulls out of shape and deforms a bit when the laces are tied. 2 eyelet fastening. Dainite soles.
Enzo Bonafe for Skoak - Utah Grain Leather, UK 9.5E, approx, £560 RRP. Gold Utah hatch-grain, noticeably thicker and stiffer than the Tricker's leather. I think the stiffness works against the boot design here - when tied up they do push against the ankles rather than flexing. 3 eyelet fastening. Dainite soles.
Edward Green Banbury - Mink Suede, UK 9.5F, £1,120 RRP. Mink suede, super soft. If you've not handled pricier suede shoes you might think suede is all born the same, but this feels noticeably silky to the hand compared to my old Foster & Son's, and the experience is reflected with more comfort on the foot. 3 eyelet fastening. Dainite soles.
John Lobb - UK 9.5E, £1,100 RRP. An aubergine-plum calf leather - not really sure if they're museum calf or just quite old with a lot of patina. Quite rigid, but very good for unfriendly weather. 2 eyelet fastening. Rubber soles.
What is a Chukka boot? And why aren't you calling it a desert boot?
A chukka boot is an ankle-height derby boot with 2 or 3 eyelets, or perhaps a buckled strap. It's probably made of soft leather or suede and is likely to be brown, beige, or one of the vivid rainbow of possible shades of browny-beige or beigey-brown.
Desert boots meet the above criteria, but also have a light crepe sole. I personally hate crepe soles, which is they aren't represented here. Supposedly the Chukka design originated from WWII soldiers who wanted a tightly laced but lightweight design that would keep the sand out (by lacing at the top) but be easy to wear -thus the "Desert Boot" name.
So in summary - all Desert Boots are Chukkas, but not all Chukkas are Desert Boots.
Design differences
So how much variation can you get from a well-established design before it's... you know, something else?
Number of eyelets - this can only really be 2 or 3 sets, and overall two eyelets is easier to do straight lacing on. Any more and they start to become ankle boots. Straight lacing can be done on 3 eyelets, but requires running some of the lace back around and doubling up and can be a pain to loosen and tighten. Since it's a short boot all pairs of eyelets will be used for lacing, unlike some taller boots where you might skip the top set
Toe shape - rounded for a more casual look, pointed and slimmer for a more dressy look
Quarters shape - quite a niche detail, but look at the point where the quarters and vamp meet - pointed in the Tricker's cut curved to various extents on the other boots. You might just get a single row of reinforcing stitching as on the Enzo Bonafe, a more intricate downward angled L-shape as on the Edward Green, or a more decorative half-circle like the John Lobbs
Backstay shape - is the backstay straight or does it taper towards the top? The Tricker's backstay is noticeably wider at the base - this doesn't make a huge overall difference in appearance but it does look more squat than the slimmer section of the Enzo Bonafe. The John Lobb here don't have a separate backstay panel - they have a kind of austerity effect with stitching where the backstay would be
Height - the backstay image also clearly shows the range of height - the Tricker's are about as low as a Chukka boot can be, around the same as a hi-top trainer. The John Lobb are noticeably taller, moving into ankle boot height
Edge stitching - the Tricker's have an additional set of three rows of stitches parallel to the edge of the quarters, as well as an extra row along the topline which is also found on the John Lobbs
Sole material - Dainite is my preferred sole for Chukka boots, though I know it has a bit of a mixed reputation in terms of being hard to walk and not great for the rain. Compare the slightly rough and ragged stitch on the Enzo Bonafe soles (it even cuts through one of the Dainite stud sections) vs. the far neater Edward Green soles.
Lined or unlined - all of the boots are lined except for the Tricker's. It works well in their favour, and makes them feel a bit more casual (and comfortable)
Conclusion
Maybe a surprising one here - by my favourite pair are the Tricker's - they don't photograph super well because the unlined leather gets pulled slightly by the shoe trees, but they are supremely comfortable and the shorter height and round toe suit the overall casual purpose of the Chukka design better than the other models.