There are four main categories of shoe – Oxford, Derby, Monk and Slip-on – and that is usually the order in which they are considered to fall in terms of formality. A lace-up Oxford, usually cleaner and sleeker than a Derby, is the most formal of the bunch, while a casual Slip-on, which can be discarded at a moment’s notice, is the least. It’s not a bad general scheme to start from. But it can be very misleading.
The biggest reason is that there is so much variation in the stylings of each. A Oxford varies from a black whole-cut – sharp and smooth and understandably elegant – to a tan full-brogue with double sole – bedevilled by detail and layers of chunky leather. A Derby need not be less formal. One with high lacing and fewer eyelets – just three say, or even two – has a very smooth and clean look to the two and vamp that has far more in common with the first of those Oxfords than the second.
Indeed, how many eyelets a Derby has and therefore how much of the facings are visible under the trouser leg is probably the key to determining how casual a version of the style it is. Fewer eyelets = more formal. Unless of course it is brogued or something similar, which does happen.
The defining characteristic for an Oxford is the amount of broguing it has. And it’s not hard to work out which of the various brogue variations (usually express in fractions) is the most or least formal. The more stuff there is on the shoe, the more casual it is. Toe-cap, wing-tip, medallion, brogued seams (some or all), heel counters and broguing elsewhere (some like thistles on the facings for a reason I have yet to fathom. I think it’s just a desire for individuality. Which is certainly achieved.)
So the more stuff on an Oxford, the more casual. And at some point the Derby and Oxford pass each other on the scale, as the former’s facings disappear beneath the trouser and the latter becomes bogged down (appropriate phrasing!) in brogued additions.
For the Monk shoe – defined by its buckle and originating from single pieces of wrapped leather worn by medieval monks, for those that don’t know – its defining characteristic is the nature of the buckle. On some Monks, the strap falls across the middle of the shoe in a wide, lazy slap to any ideas of elegance. It is perpendicular to the flow of the shoe, stops any ideas of movement in their tracks and reminds many men of buckled shoes worn by schoolgirls. It is justifiably reviled by those men.
At the other end of the scale, there is a strap that is thrown back down the line of the shoe, almost parallel to the sole. Edward Green’s Oundle, a personal favourite, is a good example of this. The front of the shoe is quite uninterrupted and contains plenty of room for colour, antiquing and patina to shine. It can even cope with a bit of broguing (as the Oundle) has, and retain its rarefied air.
Finally, the Slip-on. It becomes more formal the more it looks like an Oxford and the less it looks like a Slip-on. GJ Cleverley’s famous model with fake leather laces is a classic example, marrying up the two ends of the theoretical scale and confusing anyone that tries to defend that system. Foster & Son also does a bespoke model that achieves formality by looking like an Oxford or a Monk, just devoid of any laces or strap.
If you are trying to decide which model of shoe is best suited to the formality of your outfit, therefore, bear the scale in mind but pay much more attention to the model’s defining characteristic.