As you squelch into a puddle amidst November drizzle, thoughts turn from the robustness of your outerwear to the viability of your shoes. This is the time of year to bring out the big guns; before school term started, a young boy would always be kitted out with a pair of what your mother would term “good shoes” to see him through; the arrival of winter calls for much the same. A “good shoe” denotes reliability, form and function; stepping out on a brisk winter morning in a stately pair can’t fail to put a sartorial spring in the step, but which variety should you opt for?
Winter shoes tend to fall into two camps; smart and solid, and functional and outdoorsy. The variety most men - particularly in their corporate guise - are wise to veer towards is the former: sturdy Derbys, upright Oxfords and heavy duty brogues that will see you through hail, sleet and sheeting rain.
Tarvin brogues, £380, church-footwear.com
It’s the brogue that’s perhaps the most hardy in inclement weather. A proletarian worker of a shoe, it evolved in the peat bogs of Ireland when labourers punctuated their leather shoe with holes to allow water to drain through them, before graduating into the shoe of choice for the landed gentry. Today, brogues act as a midway point between functional and decorative, and are best suited to wool suits or crisp jeans thanks to their (very slight) ornate design.
A sleeker, more corporate affair altogether, the Oxford takes its name from those dreaming spires. A smart mode of shoe that evolved at the city’s eponymous university in the 1800s, it’s a perennial and relatively minimalist affair. Look out for a version with Goodyear welted soles (Church’s specialise in this) for extra durability.
Bradford Derby shoes, £420, crockettandjones.com
Its brother, the Derby, evolved in the 1800s as footwear for sporting pursuits. It differs in that the laces are sewn underneath the vamp (the upper leather part) as opposed to an Oxford, which conceals them underneath. It makes the shoe appear more ‘open’ and slightly less upright and formal.
That said, they look pin sharp with tailoring and a chunkier sole will bring them bang up to date. Finally on the smart footwear front, monk strap shoes are a solid winter investment thanks to their buckle design, they look and feel protective and sturdy, as well as a tad ceremonial; the straps were evolved by monks in the 15th century for adjusting their shoes according to their manual tasks.
And while boots might denote a certain ruggedness, there’s been a bubbling trend towards pairing them with smart tailoring; a streamlined pair of Chelsea or lace-up boot in chocolate leather tucked neatly beneath a hem takes the formality out of suiting ever so slightly. The weather might be turning, but it’s time to put your best foot forward.
For more in the How To Dress Well series visit https://www.telegraph.co.uk/men/style/