Any well-heeled gentleman knows that shoes make the man. The right footwear can exude elegance, infuse a splash of personality, or give that formal suit a sporty spirit. And while enthusiasm for everyone’s favourite accessory runs deep, how much do you really know about shoes? Below, we test your knowledge, breaking down the 10 styles that should form the quite literal stepping stones of every well-rounded collection. From settling the difference between an oxford and a brogue once and for all to hashing out the history of some of our favourite pairs to slip on, consider this your cheat sheet to all things shoes.

We also list our favourite bespoke purveyors, because sometimes even the best brands (don’t worry — we’ve listed those, too) can’t satisfy your exacting tastes. So, read on to discover our definitive shoe guide. Apologies to your wallet in advance.

Oxfords

Berluti Oxfords Photo: Courtesy Berluti

A basic black pair of oxfords will take you far in this life. The lace-up style has been a go-to dress shoe since the courtiers at Scotland’s Balmoral castle first wore it in the late 18th century. It was then incorporated into the student uniforms at Oxford University, lending it the name it carries today. Classically sleek, they are characterised by shoelace tabs called eyelets that are attached under the vamp (the section of the shoe’s upper stretching from the toe to about the middle of the foot) — anything attached above is classified as the oxford’s slightly more casual cousin, the derby. It bears repeating that you can’t go wrong with classic black leather — which, if the style features minimal detailing, will pair easily with everything from tuxedos to dark trousers. A pair with a toe cap (the seam that bridges across the shoe at the widest part of your foot) would look right at home in the C-suite.

Brands to Know: Despite the shoe having a distinctly British heritage, brands based on the continent often do it best. Look to Berluti for oxfords with minimal seaming, which allows their beautifully patinaed leather to take center stage. For a dose of personality, lace up a pair from Corthay, as many of the brand’s already unique styles can be customised with unique leather finishes and dandy laces.

Brogues

George Cleverly Brogues Photo: Courtesy George Cleverly

Though “brogue” conjures up a very specific type of shoe — think oxfords with intricately decorated uppers — the term actually refers to a technique by which leather is perforated with tiny holes, often arranged in flowing patterns that mirror the geometry of the foot. Today, broguing is typically used to give any shoe, from your standard lace-ups to chunky Chelsea boots, some aesthetic kick. But the technique has humble roots: it was originally devised in the 18th century to allow water to drain from the shoes of those slogging through the marshy Scottish and Irish terrain. The style remained the domain of country houses until the early 1900s, when the then Prince of Wales was spotted wearing them while out playing a round of golf. From there, it inched its way into the workday wardrobe of those whose feet were planted firmly on dry ground, adding an artistic element when wearing more demure suits or dressing up dark denim.

Brands to Know: Family-owned brand George Cleverly has a range of brogue styles, but it does formal-leaning brogues especially well. Go for the signature chisel-toe shape to add a bit of masculine edge to the model, or lace up a pair of the brand’s classic wing tips (a swooping line of perforations that forms a “W” just below the toes). Santoni offers styles with a bit of a subversive twist — think ombré leathers and styles that feature perforations almost all the way through, a wink to the shoe’s origins.

Monk Straps

Santoni Monk Straps Photo: Courtesy Santoni

Likely developed by monks (hence the name) as an alternative to sandals once winter set in, these buckled shoes have come a long way since their medieval origins. Today, they are a more sophisticated alternative to the oxford and have the uncanny ability to look either sharp or relaxed, depending on the materials with which they are made. Single-buckle models in richly polished leather are a stylish way to step out of the formal-shoe norm, and they look especially powerful when paired with a double-breasted suit or sleek shawl-collared tuxedo. Their double-buckled brothers appear slightly more casual, especially when they are made of buttery-soft suede, and can work nicely with both more relaxed suits — think slim-fitting gray or unstructured navy — and jeans.

Brands to Know: When it comes to a classic single- or double-buckle monk strap, you can’t go wrong with a pair from John Lobb or Ralph Lauren. Both brands carry styles that will pull their weight in your closet for years to come, the former made with a sharp British sensibility and the latter with an ever-so-slightly more relaxed American flair. If you crave something a little bit bolder, Santoni’s colorful styles (which can be customized by pairing together whatever two leathers your heart desires for the upper and the straps) are playful without losing an ounce of refinement.

Loafers

Gucci Loafers Photo: Courtesy Gucci

Originally worn by Norwegian fishermen, the blueprint for today’s loafer was almost simultaneously co-opted by preppy American co-eds and the English upper crust in the late 1920s as the casual shoe of choice (sneakers, after all, had only just been invented). Gucci helped elevate the style when it introduced the now-iconic horsebit loafer in 1953 — spawning generations of copycats and countless knockoffs. Over half a century later, the Italian brand still makes the classic style, though it and many others have also branched out into thoroughly unstuffy versions of the often WASP-y style. Socks are no longer required (though that debate still rages on with surprising intensity), and modern variations done in an unexpected color, punched up with often over-the-top embellishments, or made even easier to slip on with step-down backs offer playful ways to dress up your nine-to-five.

Brands to Know: Besides Gucci’s sweeping range of loafers both classic and decidedly not, almost every brand does loafers well. Tod’s is another classic option — its soft Gommino driving shoe walks the line between true loafer and dressed-down moccasin, though it also does more traditional loafers well. Salvatore Ferragamo does, too, offering a range of variations on the classic horsebit embellishment.

Smoking Slippers

Christian Louboutin Smoking Slippers Photo: Courtesy Christian Louboutin

Made famous by men who have little else in common — namely, the Pope and Hugh Hefner — smoking slippers, obviously, represent very different things to different people. The former inherited the red velvet slippers he wears as part of a centuries-old uniform, while the latter used them to leverage his personal strain of louche interests into a full-blown cultural movement. Either way, the style, which originally was worn inside with a pipe in hand by the likes of Prince Albert, quickly became a sexy replacement for buttoned-up oxfords or monk straps for a certain kind of rakish man. They have become a common black-tie option over the past 50 years, but even the most demure pairs still make a serious style statement when paired with an expertly tailored tuxedo or denim.

Brands to Know: For a model like the ones that Prince Albert would have slipped on before his evening scotch, look to Larusmiani’s selection of classic velvet slippers, which come in a range of colors. Jimmy Choo and Christian Louboutin do the modern, more opulent version of the shoe extremely well — with options ranging from silky satin outfitted with tassels to eye-catching slippers adorned with limited-edition and, for some, highly collectable patterns.

Lace-Up Boots

Bally Lace-Up Boots Photo: Courtesy Bally

Though lace-up boots have been worn by nomads, knights, and workmen for centuries, the history of the style is muddled at best. What is sure, however, is that Prince Albert once again played a role in turning the previously purely practical shoe into one of the most popular styles of the day when he commissioned a pair of lace-up boots that would keep him dry while walking around the grounds of Balmoral castle, while being fashionable enough to also wear inside. The style immediately took off, with men pairing sleek versions of the boot with their best suits. And while we would certainly recommend adding a dress boot to your wardrobe (keep it classic with a rich black leather pair), you’re likely to get much more mileage out of a pair that sticks closer to the original’s workwear roots. Look for one that mixes form with function, marrying thick soles that will keep you high and dry on even the slickest of days, with uppers that feature elevated details like broguing or softly pebbled leather.

Brands to Know: Swiss brand Bally got its start in the 1850s making finely crafted shoes, and lace-up boots were reportedly some of the first styles the house made. Today, you still can’t go wrong with one of its designs — the label makes both dressier styles inspired by Prince Albert and mountain-ready pairs. English shoemakers Edward Green and Grenson also make sturdy lace-ups that are still sharp enough to pair with wool trousers for winter days at the office.

Chelsea Boots

Saint Laurent Chelsea Boots Photo: Courtesy Saint Laurent

Another style that we can thank Victorian England for, Chelsea boots — characterised by their stretchy side panels, snug fit, and low heel — were originally commissioned by Queen Victoria, who wanted a pair of shoes she could easily slip on and off. A century or so later, the swinging Mods that would hang out in London’s Chelsea neighborhood revived the previously stuffy style as part of their rock-and-roll uniform (the style also appeared, most visibly, on the Beatles), a connotation that the boots haven’t yet shaken. Pair them under a suit for a subtle kick of personality on your nine-to-five, or with dark denim and your favorite vintage band T-shirt on casual days.

Brands to Know: Saint Laurent’s lineup of sleek — and often racy — Chelsea boots are your best bet if you are looking for a pair that fully embraces the style’s rock-and-roll roots. Church’s also makes Chelsea boots that nod to this side of the style’s history, embellishing its designs with subtle brogues and rendering them in rich suede. Berluti does them well, too, highlighting their classic minimal construction with ultrafine leather.

Sneakers

Feit Sneakers Photo: Courtesy Feit

No shoes inspire devotees quite like sneakers do. Invented in 1917 by Converse (the brand’s iconic low-top is widely regarded as the first modern sneaker), the athletic style quickly became a favourite casual shoe. It wasn’t until the late 1980s with the explosion of Nike’s Air Jordan into mainstream culture that the shoes became the full-on style statement they are today — inspiring collectors to line up for hours to get their hands on a pair and driving up resale prices for those who couldn’t get them in store to dizzying heights. Luxury brands quickly capitalised on this new market, drumming up versions of the athletic shoe elevated by buttery-soft leather or downright flashy details. Today, you can get away with a sneaker just about anywhere — though we’d suggest leaving your flashy collector’s pieces for the weekend and sticking to sharp leather styles at the office (which are best paired with pants that are ever-so-slightly cropped).

Brands to Know: Besides the classics — think Nike Air Force 1s or Adidas’ Stan Smiths — you can’t go wrong with a pair of sneakers from Harrys of London or Feit. The former takes classic shapes and renders them in candy-coloured leather, while the latter makes its minimal creamy white, tan, or all-black pairs out of single pieces of leather. On the designer front, Gucci’s Ace sneaker has become one of the brand’s most easily recognisable designs, thanks to its perfectly punchy green-and-red-stripe detailing.

Espadrilles

Tom Ford Espadrille Photo: Courtesy Tom Ford

Characterised by their soft canvas uppers and jute rope soles, espadrilles have been worn for nearly a millennium in the Basque and Catalan regions of France and Spain. The casual slip-on was made famous by Pablo Picasso and Salvador Dalí, who were often photographed wearing them in the 1940s as a nod to their Catalan heritage (which, at the time, was a visual code for their anti-Franco politics), quickly becoming part of the mainstream fashion thanks to its casual but not overly dressed-down look. The style was first elevated by Yves Saint Laurent, who partnered with Lorenzo Castañer (whose namesake brand still makes the style today) to make a pair that swapped standard canvas for luxe silk. That said, you don’t need silk to elevate the humble style, as today many designers do versions in more practical leather and suede that are equally chic.

Brands to Know: When it comes to adding a luxe twist to the classically casual style, brands like Tom Ford and Brunello Cucinelli do it well — both rendering the shoe in soft suede, often in a large variety of colours (though we’re partial to pairs done in neutrals like navy, tawny brown and yellow). Spanish leather brand Loewe also makes some of the best designer versions, leveraging the history of the shoe playfully.

Sandals

Bottega Veneta Sandals Photo: Courtesy Bottega Veneta

Likely the first kind of shoe that our ancestors ever slipped on, sandals, with their simple, flat soles and straps, have a history that can be traced back thousands of years. They’ve come in and out of fashion for men — and are often seen as only acceptable if you’re going to spend all day lounging by the pool. That said, having a solid pair of slides that can take you from the beach to the bar is an essential (even if you’ll only ever wear them on vacation), and there are plenty of pairs ranging from simple to statement-making. Look for a style that provides more coverage with wide, criss-crossing leather straps, or lean into the shoe’s Grecian roots by buckling on a pair that would look right at home on the shores of ancient Mykonos.

Brands to Know: Though you can’t go wrong with a pair of plain leather slides, Bottega Veneta often carries styles that feature luxe upgrades — think intricately woven intrecciato leather straps. Ralph Lauren and Jimmy Choo both also carry solid options, often leaning sportier (and therefore all the better for the pool) thanks to their squishy rubber soles and wide, single straps.

Best Bespoke Shoemakers

Atelier sur Mesure Bottier Photo: Courtesy Berluti

Many of the brands mentioned above have histories rooted in bespoke — after all, it was primarily how shoes were made until the invention of mass manufacturing just over a century ago. The following eight labels all carry the torch of the bespoke shoe, proving that age-old cobbling techniques still hold water in the modern world — especially when they can allow you to build the shoes of your dreams.

Stefano Bemer

Florentine cobbler Stefano Bemer has been a well-kept secret of some of the world’s best-dressed men since the 1980s. Today, the brand — which can craft everything from sharp split-toe loafers to special-order sneakers in everything from calfskin to stingray — is quietly expanding, introducing ready-to-wear styles in case you just can’t wait the 20 weeks to have your bespoke creations delivered.

John Lobb

British brand John Lobb has been making fine bespoke shoes for more than 150 years, outfitting everyone from princes (the house holds a Royal Warrant) to Aristotle Onassis in its supple monk straps and oxfords. Orders are crafted over the course of nearly a year and require at least three fittings to ensure the fit and aesthetic are exactly right. Once that pair of exotic-skin derbies are in your closet, you can expect to get at least 20 years’ worth of wear out of them.

Corthay

Certainly not for sartorial wallflowers, Parisian atelier Corthay specializes in bespoke shoes with personality in spades — oxfords rendered in subtly patinaed maroon leather and electric-blue suede tasseled loafers, or really anything else you can dream up. Founder Pierre Corthay was awarded the prestigious Maître d’Art by the French government in 2009 and is the only men’s bootmaker to ever earn the designation.

George Cleverly

Though known for shoes with a powerful chisel-toe shape, George Cleverly can craft styles to almost any C-suite exec’s taste (though the brand also counts rock stars and media moguls as some of its devoted clients). The process still employs traditional techniques of bespoke shoemaking used in the early 19th century, and fitters travel around the world constantly to take measurements and deliver shoes to clients that can’t make it to the brand’s London headquarters.

Gaziano & Girling

Out of their Savile Row and New York City outposts, the experts at Gaziano & Girling spin classic styles — sleek oxfords, single monk straps and lace-up ankle boots — into highly personal creations. In a process that can take up to 16 months, the cobblers will source that perfect snakeskin to use as an accent, carefully position brogues to flatter the individual lines of your foot, and spend countless hours working the patina of the leather until it is exactly what you want it to be.

Roberto Ugolini

The craftsmen at Roberto Ugolini, located just off the Piazza San Spirito in Florence, have put the city’s leather-working tradition to highly individualized use. Specialising in shoes with creative flair, the brand can craft everything from patent-leather and Bordeaux suede oxfords that perfectly pair with your favourite tuxedo, to mixed-media monk straps that complement ornate brogue detailing with pared-back twill.

Berluti

Though the Parisian house has leveraged modern technology to make many of its shoes customisable with the click of a few buttons, Berluti still operates a traditional bespoke service out of its boutiques around the world. Master shoemakers will help clients pick styles, soles and leathers that best fit their specific lifestyle and personal tastes and will then let them run wild with design elements — selecting patinas, designating elements to be tattooed, or choosing accents of exotic skins, all of which are sourced with respect to preserving endangered species.

Casa Fagliano

Based out of Hurlingham, Argentina, the experts at family-owned Casa Fagliano have upheld aristocratic traditions of bespoke polo boots since 1892. Today the house sends its fitters and cobblers around the world to fit clients attending the most prestigious polo matches, taking orders for everything from lace-up ankle boots to sleek, knee-high leather riding boots. If you are not an expert rider, the brand has also leveraged its boot-making heritage into sturdy, precisely designed oxfords, monk straps and derbies.