Know your Derbys from your Oxfords

Timothy Barber
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WHILE it’s tempting for a chap to slink to work each day in the same tatty lace-ups he’s owned for years, a pair of fine, handmade English shoes is a worthwhile investment for any City gent worth his salt. In fact he should have several, ensuring that each lasts longer and that he can vary his look while remaining effortlessly dapper.

According to Andreas Kuschel, a Bavarian with a passion for English footwear who manages plush Jermyn Street shoe shop John Lobb, the basic shoe that every City chap should own is a black Oxford – meaning a closed-lace shoe – with a toe-cap for added formality. “It’s the classic elegant business shoe for wearing with a suit, and always will be,” he says.

The key shoe styles (see below) come in any number of shapes and variations, but for proper English elegance avoid choosing anything too square in the toe, or with a rounded toe that ends too abruptly – it simply looks boxy and graceless. An option that’s on-trend at the moment is the chisel toe, in which the shoe tapers towards a point, and is then gently squared off at the tip. “In recent years suits have gone more fitted and narrow, which means you’re showing more of your shoe, and the slightly elongated chisel toe really suits this,” says Kuschel.

While long, pointy shoes beloved of hipsters can look too dandyish in the City, Kuschel says the tendency among a lot of men is to wear shoes that are too short. “People have this mindset that where their toe comes to is what determines whether the shoe fits,” he says. In fact, the key is in how the shoe sits around the middle of the foot – Kuschel likens the desired effect to a firm handshake, in which the centre of a person’s hand is gripped firmly but they can still move their fingers. In the same way, toes should be free while the middle of the foot is supported securely. That will ensure the perfect mix of comfort and style.


For those who fancy stepping out in something different, John Lobb is holding a “By Request” service from today until next Saturday, in which you can order key styles in varied mixes of colours, leathers and soles of your own choice, at no extra cost.
John Lobb, 88 Jermyn Street, SW1Y 6JD.

People often assume that “Oxford” refers to a laced shoe with a toe-cap, but it actually describes the closed style of lacing (as opposed to the open, Derby style) in which the flaps holding the laces are stitched together at the bottom for a tidier effect. Effortlessly smart, it’s the ultimate English formal shoe.
Left, Black Cap Toe by Lodger Footwear, £550,

The open lacing – the lace flaps don’t join – makes the Derby more informal than the Oxford. This brown suede version is pretty relaxed, but suede with a suit is a growing trend (though perhaps still unwise in the City). It’s seen as a European fashion, but it was the Duke of Windsor who did it first.
Left, Tiverton Derby in tobacco suede by John Lobb, £630,

Whether you go for the full brogue – with the “wing-tip” w-shape toe cap – or an Oxford with brogue punching, a few spiralling holes add textural style that’s subtly flamboyant. They work particularly well with a pinstripe suit, with a nice contrast between the linear suit pattern and the brogue swirl.
Left, Worcester brogue by Russell & Bromley, £195,

Monk shoe
These make a snazzy style statement while retaining the crisp formality of the Oxfords. They’re particularly smart when worn with narrow-cut trousers, but avoid mixing them with turn-ups, since their streamlined look will suddenly seem bulky. They look good in suede, and two buckles adds extra zip.
Left, William II monk shoe by John Lobb, £655,

Normally an informal shoe, particularly as worn on the Continent, the slip-on can still be worn smartly in more pointed, black-leather versions. You wouldn’t sport them in the boardroom but they look sharp when worn selectively, and tassels are back in fashion for adding formality and character.
Left, tassel loafer by Russell & Bromley, £175,