There are two basic principles to follow if you want to own a small men’s shoe collection that is adaptable enough to cover all of the main varieties of men’s shoes. The first is to abandon fashion in favour of timeless styles. The second rule is to spend as much money as possible. Because the old adage is true, consider quality rather than quantity. People frequently notice your shoes first, especially if they appear to have been around the block a few times.
Because the goal is to have as few couples as possible, there is one extra rule: be cruel.
Some of our favourite styles aren’t listed below because they’re not necessarily men’s shoes if you’re on a tight budget or attempting to save room. Hiking shoes? It’s nice to have, but it’s not necessary. Monk straps, pool sliders and even high tops fall into this category.
But, whatever your style, budget, or plans for the next 12 months, if you own a pair of well-made shoes in each of the following designs, you’ll be tastefully shod in just about every social occasion, from workplace to gym to bar. You’ll never have to put your foot wrong again.
Minimal Sneakers
Although chunky trainers are popular, the minimalist trainer is the true wardrobe hero. This simple sneaker, based on a retro tennis shoe, has become an essential component in most of our wardrobes in recent years, and it should be in yours as well. The genuine article lacks evident sports logos or branding, heavy treads or air-cushioned soles, is constructed of leather (real or imitation), and should never be confused with plimsolls.
Consider these your go-to trainers because their main selling point (especially in white) is their adaptability. Wear them with tees and chinos, jeans, shorts, and casual tailoring from day to night. They do, however, have a use-by date: once they start looking past their prime, consign them to housework or tasks. Never use them for exercise, and keep them as fresh as possible – put some deodorising insoles in on the first day. Some of the better examples are by Common Projects, Axel Arigato, C.QP, and Adidas Stan Smiths.
Oxford Shoes
Oxford shoes are the traditional ‘school’ shoe, used only for business and ceremonial occasions such as weddings, funerals, christenings, and job interviews. Basically, whenever you’re wearing a nice suit or a black tie. It’s commonly seen as the shoe for ‘professionals,’ and it used to be a dress requirement for work at city banks. Perhaps a touch monotonous, but a reliable set of hands (or feet) and the workhorse in your footwear collection if your job necessitates daily smart clothes.
The name is derived from a style of half boot that was popular at Oxford University in the 1800s, but most Oxfords are now seen in shoe form. These are ‘close-laced’ shoes, which have the inside and outside quarters stitched under the vamp (the piece of leather that makes up the front of the shoe) and the tongue stitched separately. A high-quality pair is an excellent investment because they will never be out of style. Crockett & Jones, Church’s, Loake, Tricker’s, and John Lobb make some of the finest specimens in England.
Derby Shoes
The Derby shoe is the chunkier relative of the Oxford shoe. It’s both a ‘in-between’ shoe and the pinnacle of smart casual footwear. They can both sharpen and loosen a suit and are basically standard equipment for flat white-wearing creatives.
The difference with an Oxford is in the construction; the tongue is part of the vamp and the quarters are stitched to a point on either side of the vamp – this is known as ‘open lacing’. Another important component of the Derby is the sole, which can be leather or rubber for increased traction and durability. The upper is stitched to a leather strip called the welt, which is subsequently stitched to the shoe’s insole. This game-changing method made shoes waterproof and today, Grenson is a go-to brand for its triple welted Derby.
For those reasons, Derbies are practical shoes that look good with pretty much everything. The simpler the model (without brogue details, single welt) the more versatile the shoe will be. On a practical note, the shape of the Derby is also more forgiving to wider feet with a higher in-step.
Espadrilles
The espadrille is the oldest form of shoe on the market, having been there since the 14th century. It’s a common type of footwear that can be found cheaply in marketplaces throughout Southern Europe, but there are also more expensive, designer versions available.
Espadrilles are more durable and adaptable than flip flops, making them ideal for short walks along sandy beaches and beyond. That means you can wear them from the beach to the bar and then explore the ancient town. The canvas uppers are breathable and cover the front of the foot, which is useful if you haven’t trimmed your nails. Espadrilles look great with linen, beach wear, shorts, chinos, light jeans, and can even be worn with a summer suit on special occasions, such as a poolside wedding, but never, ever with socks.
Running Sneakers
Have you ever heard of Carolyn Davidson? We have our doubts. So you might be startled to hear that you are currently wearing one of her designs. Davidson created the Nike Swoosh logo in 1971 for the delightful amount of $35 (yes, she got ripped off). The athletic shoe market is now worth billions of dollars, which hasn’t gone unnoticed by high fashion designers, who have responded with designer (overpriced) versions and numerous partnerships to attract younger buyers.
You can wear a variety of trainer types with virtually anything these days, but unless you’re comfortable pushing the fashion envelope, stick to denim and sportswear as safe bets. Whether you’re a sneakerhead or just prefer the comfort element, having a good pair of gym shoes on hand – New Balance are a terrific alternative. Proper running shoes provide adequate support in key areas and can help prevent the feet (especially if they are flat) and ankles from damage. (And don’t worry about Carolyn; she eventually received a diamond ring and 500 Nike shares.)
Brogues
A brogue shoe is a type of Oxford shoe with ornamental perforations throughout to give it a more trendy edge. The characteristic shape of the style was originally intended as an escape valve for bog water, which was popular among Irish farmers who spent half their working day stomping through waterlogged fields.
Practicality gave way to fashion, and the brogue shoe is today a favourite of office workers and well-dressed men everywhere. A pair of brogues is a shoe that every man should have in his shoe collection. Trickers, Church’s, Ted Baker, and Dune London all create elegant pairs.
