About the monk strap
The monk strap shoe dates back to the 15th century, as a strapped sandal favoured by monks for their various manual labours and assorted monkish duties. From such humble beginnings, the monk strap went on to enjoy some popularity as the de facto shoe for the iGent / Pitti Peacock crowd. After some ridicule and market oversaturation, it's since seen a bit of a decline in popularity.
As a shoe model, the monk strap exists in a strange place on the formality spectrum. Frequently featuring a plain captoe, they can appear relatively dressy, but the presence of the buckles (sometimes multiple buckles in more extreme cases) diminishes this dressiness. This broad window of formality makes them a good choice for men who really only need dress shoes occasionally... people who would look at you like you're an idiot for using the words "formality spectrum" (you know, normal people).
From experience they can also be somewhat eccentric in the fit - the section that is buckled over the top of the foot can dig rather awkwardly when flexed if the fit isn't just right, and the strap can also cause the topline of the shoe and the tongue to dig into the ankle. That said, the utility of being able to tweak the exact fit with the buckle (which was the reason for their original popularity with manual labourers) remains a helpful aspect.
The monk strap in the current shoe market
In spite of my earlier unkind ridicule of the style and its association with Pitti Peacocks, the monk strap is still well represented by big British makers. The William is one of John Lobb's most enduring models but they also have dressier versions such as the Jermyn II from their Prestige collection.
Likewise, Crockett & Jones have an expansive selection of monk strap models, with 20 available at the time of writing on their website. These run the gamut from single strap and rather dressy cutaway designs to intentionally chunky models like the Whitby below:
In fact you'd be hard-pressed to find a major maker that doesn't offer any monk straps.
What to look for in a monk strap
The main considerations particular to monk straps when shoe shopping (aside from the usual aspects of construction and leather quality, which I've written about at length in other posts):
Number of buckles - my personal taste has shifted to the single buckle monk strap, though double-buckled versions are very common. Any more than that (a triple or even quadruple buckle) tend to fall into costume territory (and are a tremendous pain to do up)
Buckle angles and cutaway - where multiple buckles are used, there is a design consideration of whether the straps are set parallel or if they splay outwards. In the case of a single buckle design, this becomes a choice of whether the strap sits across the top of the foot, or if it uses a more refined-looking cutaway design to run more horizontally and parallel to the sole
Hardware finish - unlike most dress shoes, monk straps have very obvious metallic components in the buckle. These will mostly be silver-toned or golden, polished or maybe antiqued. My own preference tends towards an unpolished brass - more fashion-forward designs will probably use a polished silver or palladium. I suppose the usual rules about matching the metal with your belt-buckle or watch should apply here, if you care about that sort of thing. Which I don't
Toe design - as mentioned above, plain captoes are very common for monk straps. Apron fronts (with or without a split-toe) are worth considering here too
I've not owned all that many monk straps, but I've detailed them a bit below:
Church's (model unknown) single strap split-toe - a recent acquisition from a charity shop, these have proved pretty worthwhile. The buckle on these is elasticated, which makes for a comfortable fit. I enjoy the split-toe front too. Sadly I have no idea of the model name, as the handwriting used on Church's size labels inside the shoes is abysmal to the point of being unintelligible.
Foster & Son bespoke single strap wingtip brogues - a much-restored eBay purchase, these are chunky and heavy to wear, but the cherry red leather is of fabulous quality.
John Lobb double strap suede - an appealing pair, but the aforementioned comfort issues were prevalent here. The top of the buckled vamp section tended to dig right into the instep when talking, with the tongue sitting below the topline of this section. I suspect this was done for a more elegant profile, but poor design since it made them so uncomfortable. I do have a weakness for the very dark brown suede though.
John Lobb St James single strap suede - a beautiful pair from the renowned London-based bespoke house, the design here is I think extraordinarily elegant. A shame they didn't fit well.
On buckled boots
A bit of a bonus section here, but buckled boots are worth some discussion. Generally, buckles are used in boots to secure the shaft as a supplement to lacing, as with these Crockett & Jones Aldershot, J Fitzpatrick Colville, or my own John Lobbs:
Less frequently seen are buckled Chukka boots such as this vintage model from Florsheim from Classic Shoes for Men, which is essentially a monk strap shoe with a boot height shaft. They aren't easy to pick up these days, but I personally really dig the aesthetic:
Or you might spot something more like this Crockett & Jones model, which I confess I find pretty horrible in terms of proportions and Frankenstein's monsterish in terms of design: