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Shoes should be seen as an investment, if you look after them they will last for years, when they wear out you can sent them back to the factory and they will come back as good as new.

For more reasons to buy good shoes please read our shoe basics page. This article covers the various classic shoe styles and when they’re appropriate to be worn.


A pair of black lace ups are a wardrobe staple, I often see younger Aspiring Gents sporting hideous pointed toe high street shoes made from sweat shops with plastic leather in the far east, if that’s not enough of a reason not to own a pair like that then they last 6 months and you need a new pair – that’s my rant for today! It’s safe to say that no other shoe is more elegant than a pair of black Oxford lace ups.

Classic Oxford Shoe, Knightsbridge from Herring Shoes (£175)

The level of decoration marks the formality of the shoe – the more decoration, the less formal – for example – traditionally a plain oxford is worn with a morning suit.

The word used to describe the decoration is calling brogueing. The detailing was first used in the shoe to allow water to escape when walking in the countryside, because of the history more brogueing equals less formal.

The 4 main types of oxfords and brogues from left to right from Herring Shoes: Knightsbridge (£175), Belgravia (£185), Hampstead – Semi Brogues (£175), Richmond – Full Brogues (£175)

Cheaper options are available from Loake, if you have a larger budget try Crocket & Jones, Church’s, Edward Green or John Lobb given in order of expense.

In Cigar suede the semi plain oxford brogues has a different aesthetic. Its uses are wide with jeans and shirt, Chinos and a Blazer – the smart casual shoe of choice. The shoe above is the Reading from Herring Shoes (£99.95) Barker also make a similar model.


Loafers are always less formal but some people can’t get enough of them. There are however some classics that in black are suitable to be worn with a suit and perfect with grey trousers and a blazer for visiting the club or restaurant when in town. In Cigar Suede they lend themselves to jeans or chinos.

The Tassel Loafer: Ascot II by Herring Shoes (£175)

Classic Penny Loafer: Charlton by Herring Shoes (£175)

Monk Straps

Although they shouldn’t be your first purchase, if you wear black shoes frequently and already have a collection of oxfords and loafers the monk strap is a perfect diversifier, I personally cannot get on with loafers so my next purchase of black shoes may well be a pair of monk straps.

John Lobb Williams II – The updated original designed by William Lobb.

Classically styled double Monk: Shakespeare II by Herring Shoes (£195)

Single Monk: Westbury by Church shoes (£360)

The off duty variant; if you don’t like the classic oxford then this is still a classic option. Attlee from Herring Shoes (£225)

The Chelsea Boot

The Chelsea boot originates as a riding shoe; shown above is the Coltham from Herring Shoes (£170) which is a great shoe, perfect with Jeans and a shirt at the weekend, this shoe could also be used – because of the equestrian past – with a suit at informal race meeting or with a tweed jacket, chinos and tie. The all round Chelsea boot is an ideal cold weather shoe

The Driving Shoe

Just as the Chelsea boot is the ideal cold weather shoe: the driving shoe is the ideal warm weather shoe. Great paired with chinos and a linen shirt at a picnic in the height of summer or on holiday.

No one makes the driving shoes better than the Italians so brands such as Tod’s and the original Car Shoe

Tod’s Gommino Driving Shoe (Tod’s outlet in Bicester village: £165)

Maranello driving shoe from Herring Shoes (£75)