Duelling takes — fashionable or perennially favoured — on the all-important office shoe.
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‘The Bear Option’: Velasca Milano Questurin Goodyear oxfords
Don’t let fashion pundits fool you: reports of the leather dress shoe’s demise are grossly exaggerated. In fact, circa 2026, men of all ages are rediscovering the joys of a well-crafted pair. For the ‘performative male’, horsebit loafers and mule-esque kickdowns are enjoying an extended renaissance. But bring back the Oxford, we say.
Characterised by a cleanly sewn captoe and closed laces, it is – in its pivotal details – the quintessential dress shoe. A serious article for serious operators, in need of a little pomp sans ceremony. Italian label Velasca Milano’s take is a bestseller we can rally behind. Dubbed the ‘Questurin’ (~$968), it is available in classic shades of black (shown above) and brown, along with a nattier version in midnight navy. Made in central Italy using wax-treated bull leather, these oxfords ride the rails between elegance, comfort, and durability.
The biggest selling point? Longevity.
Crafted with a technique known as Goodyearwelting, each shoe is purpose-made to be resoled – enabling potentially more than a decade of wear. That traditional construction also necessitates an interstitial layer between the upper and outsole. Over time, this mid-sole, made from natural cork, ensures the Oxford’s shape conforms uniquely to the wearer’s foot. “If the shoe fits,” indeed.
‘The Bull Option’: Tod’s Red Dot sneakers in Pashmy suede
Though the exact execution varies from brand to brand, the four-figure sneaker has become a ubiquitous item among stylish men over the past half-decade. Invariably made with a white rubber sole, suede uppers, and elasticated tongue, it is as emblematic of the whole ‘quiet luxury’ movement as a vintage gold dress watch or well-worn Vicuña sweater.
Odds are you’ll see all three worn simultaneously on a certain kind of individual: in search of a casual shoe that whispers their appetite for la dolce vita. Tod’s ‘Red Dot’ sneakers ($1,790) provide an underrated option. The Italian leather goods specialist has conceived it in 10 different colourways – one to match the carpets in each of your Gulfstreams, perhaps?
There are versions in brown calfskin leather or forest-y suede, and for something in the mould of the beige ‘billionaire’s slipper’, a sand-coloured variation in what Tod’s refers to as ‘Pashmy’. Technically goatskin, the material is treated to achieve a light, silky handle that flatters the Red Dot’s already-ergonomic design.
‘The Bear Option’: Lee Mathews x Loq Daria Mary Janes
The old biblical wisdom about putting aside “childish things” may pertain to many of the excesses of consumer fashion – Labubus, anyone? – yet the Mary Jane is not one of those. Long a staple in fashion’s neo-prep and Lolita subcultures, this fanciful take on the classic ballet flat is an efficient way to sneak style into (otherwise mundane) conversations about how to dress for work.
In collaboration with Lee Mathews, Spanish shoemaker LoQ does a great riff called the Daria ($549). These are secured with a single elegantly thin strap worn across the wearer’s in-step, set with oval-shaped silver hardware that mirrors the Daria’s soft, easy going shape. Pair these with a wrap skirt at your next weekend event, and again on a Saturday in your gnarliest painter’s pants.
‘The Bull Option’: Bottega Veneta Grace slingback sandal
Among the signature footwear styles of Fall 2026 at Bottega Veneta, these ‘Grace’ sandals are an assured option for the professional cool girl set. Made as a slingback with a diminutive kitten heel, they’ll take you from investor luncheons to the centre of clubland: hopefully somewhere underground and lavishly upholstered, to the tune of Warm Leatherette.
Available in a rustic shade that evokes Bottega Veneta’s signature ‘Fondant’ brown, we’re even bigger fans of the cardinal-red version ($4,960) – a refreshing change of pace from all the usual tropes of fog, fallen leaves, and crackling firewood in winter. Under Creative Director Louise Trotter, Bottega has burnished its reputation as a house of crafted ingenuity.
The straps on these sandals are a subtle illustration, crocheted with a torchon-style technique borrowed from the textile industry. When applied to leather, its decorative effect suggests helixes of chainmail seamlessly intertwined: modern-day armour for well-heeled professionals.
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