There are two simple rules for owning a small shoe collection that is versatile enough to cover all bases. The first: forgo fashion and hotfoot it to classic styles. The second: spend as much as you can. Think quality, not quantity because the old adage is true. Your shoes are often the first thing people notice about you, especially if they look like they’ve been round too many blocks.
Since this is about having as few pairs as possible, there’s one more rule: be brutal. Some of our favourite styles are not included below because they’re not absolutely essential if you’re on a budget or trying to save space. Chelsea boots? Hiking boots? Nice to have, not need to have. The same goes for monk straps, pool sliders and even high tops.
But whatever your look, whatever your budget and whatever’s in the diary over the next 12 months, if own a pair of well-made shoes in each of the following styles, you’ll have just about every social situation – from office to gym to bar – stylishly shod. You need never put a foot wrong again.
For Anytime, Anyplace: Minimal Trainers
Chunky trainers might be having a fashion moment, but the minimalist sneaker is the real wardrobe hero. Based on a retro tennis shoe, this simple sneaker has become an essential component in most of our outfits in recent years and it should be in yours too. The real deal is devoid of any obvious sports logos or branding, thick treads or air cushioned soles, are made of leather (real or imitation), and are never to be confused with plimsoles.
Consider these your go-anywhere kicks because their USP is versatility (especially in white). Wear them day-to-night with tees and chinos, jeans, shorts and informal tailoring. However, they do have a use-by date: that moment they start looking past their best, relegate them to loafing about the house or doing chores. Never wear them for exercise and keep them as box fresh as possible – be sure to pop some deodorising insoles in on day one. Common Projects, Axel Arigato, C.QP and Adidas Stan Smiths are some of the best versions around.
For The Smartest Occasions: Black Oxfords
The black Oxford shoe is your classic ‘school’ shoe: it’s strictly for work and formal occasions such as weddings, funerals, christenings and job interviews. Basically, whenever you’ve got the good suit or black tie out. It’s often viewed as the shoe for ‘professionals’ – in fact they used to be a dress requirement for jobs at banks in the city. A little boring, perhaps, but also a safe pair of hands (or feet) and the work horse in your footwear collection if you have a job that requires daily smart attire.
Ostensibly, the name comes from a type of half boot that became popular at Oxford University in the 1800s, but today most Oxfords will be found in shoe format. In technical shoe-geek terms, these are ‘close-laced’ shoes, where the inside and outside quarters are stitched under the vamp (the piece of leather that makes up the front of the shoe) and the tongue is stitched in separately. A high-quality pair is a worthy investment because they’ll never not work for smart occasions. Some of the finest examples are made in England by Crockett & Jones, Church’s, Loake, Tricker’s and John Lobb.
For The 9-5 And Beyond: Derby Shoes
The Derby shoe is the Oxford’s chunkier cousin. It’s an ‘in-between’ shoe, and the ultimate in smart casual footwear. They can sharpen up raw denim as well as they loosen up a suit and are practically standard issue for flat white-carrying creatives.
The technical difference with an Oxford is in the construction; the tongue is part of the vamp (not stitched on separately) and the quarters are stitched to a tab point either side of the vamp – this is known as ‘open lacing’.
The sole is another key component with the Derby: these can be leather or rubber for extra grip and durability. Either way, these are often Goodyear welted. American Charles Goodyear patented his welt technique in 1871, whereby the upper is stitched to the leather strip known as the welt, which is then stitched to the insole of the shoe. 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.
For The Dinner Date: Leather Slip Ons
This type of shoe covers a range of styles including the penny and tassel loafer. The slip on has American heritage and is synonymous with the preppy ‘Ivy League’ look and Michael Jackson’s Moonwalk. George Henry Bass, maker of the original penny loafer, founded G.H Bass & Co. in Maine in the United States in 1876. His famous ‘Weejuns’ are still the most notable style today and were based on the Norwegian farm shoe.
Going with the preppy vibe, loafers and chinos are a classic combination. If it feels too stuffy, it’s acceptable to wear loafers with and without socks – here’s an opportunity to experiment with different prints, patterns, colours – with a rolled-up cuff. It’s an easy, versatile shoe, hence its adoption by everyone from bankers to outdoor sports enthusiasts to punks and Ivy League frat boys. Today, under Alessandro Michele, Gucci’s horsebit loafer has regained the top spot as the most desirable slip on.
GH Bass & Co
For The Weekend: Work Boots
Northampton is the capital of the British shoe industry and much of its centuries old success is down to outfitting British armies and workers. Infantry needed boots on a mass scale, as did the thousands of workers toiling in factories during the industrial revolution. Most British shoe brands originate from this English county – the village of Wollaston, for example, is the original home of Dr Marten’s.
And for anywhere with inclement weather, work boots remain an essential type of shoe for tricky terrain and wet conditions, the smarter equivalent to wellingtons. The laced Derby work boot is a double-lined extension of the shoe version, and a smarter relation to the hiking boot. It looks excellent with heavy weight fabrics such as wool or tweed trousers, cropped above the ankle. Incidentally, Daniel Craig, as James Bond, wore Crockett & Jones’ Radnor boot for scenes in SPECTRE so you can be sure that in a Derby boot, you’re ready for anything.
For The Beach: Espadrilles
The oldest type of shoe on this block, the espadrille has been knocking around Europe since the 14th century. The term espadrille is French, but the origins come from esparto, the Greek name for a tough type of Mediterranean grass used to make rope, rugs, baskets and the plaited soles of this type of shoe. It’s a common form of footwear that can be picked up inexpensively from markets around Southern Europe, but pricier, designer versions abound too.
Sturdier and more versatile than flip flops, espadrilles are fairly comfortable for short distances and suitable for sandy shores and beyond. Which means you can wear them from beach to bar and then take in the sights of the old town. The canvas uppers are breathable and cover the front of the foot – a bonus if you forgot to tidy your nails. Espadrilles go well with linen, beach wear, shorts, chinos, light jeans and can even go with a summer suit on the right occasion – a pool side wedding for example – but never, ever with socks.
For The Gym (Or The Pub): Runners
Ever heard of Carolyn Davidson? We doubt it. So, you might be surprised to learn you could be wearing one of her designs right now. In 1971 Davidson designed the Nike Swoosh logo – for the princely sum of $35 (yeah, she got mugged off). The athletic shoe market is worth billions today – something that hasn’t gone unnoticed by high fashion brands: cue designer (overpriced) versions and endless collaborations to lure in younger customers.
In the 2000s Martin Margiela took a €10 runner off a Parisian market stall, scribbled on it with biro and sold it for €300 – and the cult fashion trainer was born. Other hits include Dior Homme’s ‘B01’, Valentino Garavani’s ‘Rockrunner’ and Balenciaga’s recent ‘Triple S’.
These days you can wear a multitude of sneaker styles with almost anything, but unless you’re confident pushing the fashion envelope, stick to denim and sportswear as foolproof options. Whether you’re a dedicated sneaker freak or just like the comfort factor, make sure you always have a decent pair for the gym – New Balance are a good shout. Proper running shoes give right support in the right places and can help protect the feet and ankles from injury. (And don’t worry about Carolyn – she received a diamond ring and 500 Nike shares some years later.)