Classic Shoe Styles

Classic Shoe Styles

Shoes should be seen as an investment, if you look after them they will last for years (see our shoe care guide), when they wear out you can send them back to the factory and they will come back as good as new. It’s a far better deal than buying from some online retailers that sell shoes at £30-£50 a pair. With these companies you end up having to replace them at least annually, and you run the risk of the pairs that turn up consist of two different colours or styles, and you they can’t be worn in the rain as they go mouldy when they dry out.

There are various classic shoe styles worth investing in, so we’ve put together our guide to them and when they’re appropriate to be worn. Makers to look at in increasing price order – Barker, Herring Shoes, Crocket & Jones, Church’s, Edward Green or John Lobb. Cheaper options are available from Loake and Russell & Bromley.



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, there a classic and go with almost anything. A decent pair should be your first buy and form the basis of your classic shoe collection.

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.

In Cigar suede the semi plain oxford brogue has a different aesthetic. Its uses are wide with jeans and shirt, Chinos and a Blazer – the smart casual shoe of choice.



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 is a classic but is somewhat like marmite; you either love the tassels or you hate them. The other classic is the Penny Loafer and the way to go for all you tassel haters out there.

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 they make a perfect alternative black shoe purchase for me. There are two classic styles, the Double Monk and the Single Monk.

The Chelsea Boot

The Chelsea boot originates as a riding 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, and some use them as an occasional replacement for Oxfords with a suit, though this isn’t really a correct use of them.

The Driving Shoe

Not to be confused with a loafer (though usually referred to as such), 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 are a great place to go. So is Russell & Bromley, who have many of their sued shoes made in Italy.

This article is a rework of one originally written by the author for their blog An Aspiring Gent.

Feature Image by Fancycrave from Pexels.