As with much of menswear, there exists a sliding scale of the formality of footwear that the obsessive can get caught up in if he so chooses. I think this is generally to sacrifice the beauty of personal expression to the uniformity of correctness – a correctness that doesn’t exist today and, much to the disappointment of many, never existed in the first place. (It is a similar disappointment to the revelation that Italians don’t dress particularly well as a whole, very few Englishmen wear the good suits their country is famous for, and Americans wear Ralph Lauren polo shirts but otherwise singularly fail to look like Ralph Lauren.)
However, there are some differences in shoes that are worth remembering. Here they are.
Some shoes are entirely inappropriate for some occasions, even today. You wouldn’t wear an out-welt cordovan boot to a black tie dinner, and you wouldn’t wear a velvet slipper to go tromping through the countryside. Those are probably the two ends of the spectrum of formality, and the key thing to notice is the difference in delicacy. Formal shoes are delicate, casual shoes are rough. Just like worsted and tweed, or satin and knitted wool. The point is universal.
Apply this to every type of shoe. A derby is more casual than an oxford because it has two humping facings strapped across the instep. A brogue is more casual than a whole cut because, well because of the broguing. It breaks up the line of the shoe and makes itnjagged. A leather sole is more formal; a thinner sole is more formal; a closer-cut welt is more formal. You get the idea.
This is worth remembering because there is an actual, noticeable difference in the formality of a derby with a double sole, broguing and outwelt stitching, and an Oxford, lace-up whole-cut. It’s the kind of difference that someone will notice at a job interview. Perhaps not consciously. Plus if you have ignored this part of your outfit, doubtless other elements are just that little bit too casual and unconsidered. It makes an impression.
So that’s worth being aware of. What it’s not worth losing sleep over is whether a derby can be worn with a worsted suit. For a start, there are many many types of derby. Some have just two holes and the facings are cut so high you barely see them under the trouser leg. They present merely a glorious, shiny expanse of very-formal leather. Smarter than a rubber-soled Oxford half-brogue certainly. Stating that it is not correct to wear a derby with worsted (because it is a casual, country shoe suited only to tweed or – at the most – flannel) is to draw a misleading hard line.
Second, any rule would be self-defeating, even if it were easy to define. A derby shoe is just as appropriate as a wool tie. Denying both and confining a man to worsted, silk and Oxfords is to defeat the self-expression that lies at the heart of good dress. No one who plays entirely by the rules has ever been considered a good dresser – and not because they merely stood out by innovating, but because to be a good dresser, to develop style, you have to be encouraged in your dress and feel free to revel in it. Otherwise you are merely the man in the grey flannel suit. It doesn’t matter how much I love grey flannel (and I do, oh I do), if everyone wears it and I’m being told to wear it then it cannot be stylish.
Understand the rules so you know how to break them. Understand the formality of shoes.