While double monks are perhaps the most over-discussed footwear style on the internet, single monks are perhaps the most under-discussed. My preference is for the dressier cutaway single monk – a term, by the way, I’ve just made up, so don’t go requesting that anywhere.
The cutaway monk is a single strap shoe with a more swept back buckle. The strap cuts back a bit further, towards the shoes’ quarters, and is placed a bit higher on the vamp. This creates a bold, but always correct, design that’s best worn with a dressier style and Continental European silhouette.
There have been many models. John Lobb’s Jermyn and Vale are perhaps most iconic. The Jermyn is built on Lobb’s 7000 rounded toe last, while the Vale is built on the 8000’s slightly chiseled toe. They’re both made with seamless, undivided backs but they differ ever so slightly in terms of how the straps are angled. Like their Prestige line double monk, the Jermyn III is also made with Lobb’s new buckle. LeatherSoul has versions of it in misty calf.
The other classic is Edward Green’s Oundle, which was made to replace the Stowe. Though it’s not a wholecut like Lobb’s, I find it a bit more aesthetically pleasing. The strap cuts back a bit less aggressively, but the sweep is still very rakish. Edward Green makes a very similar shoe for Ralph Lauren’s Purple Label, which for them is called the Grant. Some of these have medallions and are made in lighter colors.
Other models include Alfred Sargent’s Benson and DC Lewis’ Clayton. Cheaney, Ferragamo, and Santoni also had versions back in the day, but I believe they’ve been discontinued. In the end, I think the best designs are ones that are well balanced and proportioned – a strap that doesn’t leave the vamp totally exposed, but doesn’t completely cover it either; a buckle that sweeps back a bit, but isn’t horizontal to the ground; and a toe that’s sleek, but not overly pointed. To me, that model is Edward Green’s Oundle, but of course each man’s preferences will differ.