Three Ways To Wear Derby Shoes In 2018

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Three Ways To Wear Derby Shoes In 2018

Words by Mr Stephen Doig

27 September 2018

Reliable and versatile, Derbies look as good with a smart suit as they do with jeans and a rugby shirt.

Such are the theatrics around men’s footwear these days that even the more formal and proprietous branches of the shoe tree have been treated to some high jinks. Classic shoes, which your father would term “sensible”, have been reimagined with chunky soles, quirky panelling and sports-tech accents. The strong, silent type of the footwear roster, the Derby sits alongside its more patrician and equally English-locale-focused Oxford, the difference being that the laces on the latter are sewn underneath the vamp, or panel of leather on top of the foot, and on Derbies the laces are sewn on top, appearing open. The result is that Derbies, while smart, are a tad less upright and formal than Oxfords and more ruggedly everyday.

Which makes them an informed choice for autumn. They’re substantial enough to crunch through auburn foliage without being overly precious, but they also work harmoniously in more corporate environs. And in an age where hifalutin, bells-and-whistles sneakers the size of a small London one-bed are the norm, there’s a quiet, humble stoicism to the Derby. It evolved in the 1800s as a solid option to be worn for gentlemanly sporting and hunting pursuits, and maintains that air of reliability and versatility. It’s as easy with dark denim as it is with smart wool trousers.

Contemporary iterations might adjust the formula slightly – a chunkier sole, perhaps, or contrasting stitching – but there’s a simplicity and sense of discretion to Derby shoes that’s rare in men’s footwear today, a low-key outlier that should be in every informed wardrobe. Here are three ways we’re wearing them this autumn.


A pair of Derbies in sleek black leather will always be a failsafe, particularly with office attire. They’re polished and masculine and the classic shape complements a well-tailored suit nicely. Keep them pin sharp and gleaming so they pick up the subtle shine of a knitted silk tie or the glint of cufflinks on a shirt sleeve. They’re put-together, but durable enough to see you negotiate puddle-strewn pavements from the City to Wall Street as autumn approaches.


Take Derby shoes back to their countrified roots by opting for a pair in a rich russet shade, such as these handsome cinnamon ones by Brunello Cucinelli. A fawn soft-structure jacket will look suitably rustic. The less upright shape gives a weekend-appropriate feel, particularly alongside a scarf in autumnal hues. A grandad-collar shirt in a workwear fabric such as chambray will keep things contemporary and dynamic alongside the sedate tones.


Derbies with more heft, such as this heavy-soled pair from Dries Van Noten, work well with a more casual stance, a more elevated (quite literally in this case) alternative to sneakers that help lend form to easy denim. Pair with a low-key shirt or rugby sweater and opt for chunky socks for a deliberately off-duty stance. In fact, opt for striped socks to make a feature of your chunky Derby shoes and draw the eye southwards.