The 6 Dress Shoes Every Man Must Own

Throw out your dad sneakers.
ILLUSTRATOR Jasrelle Serrano

When they say that “shoes make the man”, one begs to ask, what have we evolved into after over half a decade of sneaker dependence? While it can be generally attributed to man’s desire for comfort and ease, or alluded to a growingly active lifestyle, a less stringent new economy, or a more permissive society, a good looking, albeit popular, pair of sneakers still has no room in the boardroom nor the ballroom.

When we’ve all grown too relaxed, gentlemen, it’s time to pick up the slack and invest in some serious shoes. So, to tie up some loose ends, we've rounded up a list of the six classic shoes any self-respecting man worth his hide shouldn’t do without.


Definition: Also known as the Balmoral, the Oxfords first appeared on the feet of the Scottish elite. Its popularity did not catch on, however, until the mid 1800s, when Oxford University students rebelled against the compulsory knee-high boots in favor of the ‘hipper’, sleeker, cut-below-the-ankle shoes. The Oxford is known for its “closed lacing” system, in which the vamp—the section of the shoe’s upper that covers the toe and instep—is stitched on top of the quarters, and the eyelet facing stitched under the quarters. Its heels are also maintained to a minimum to keep up with its low-profile sophistication.


Application: While some Oxfords tend to feature intricate broguing (decorative perforations), not all Oxfords are brogues, and this distinction can spell all the difference in its appropriation for our daily dressing.

The Whole Cut Oxford is perhaps its most snobbish iteration, constructed of a single piece of leather with no need for extra stitching or decorative details. This sparseness is best witnessed in shiny patent leather, resulting in an impressive white-tie trotter.

The Plain Oxford basically consists only of the quarter and the vamp, a study in minimalist elegance that is perfect for sober black-tie affairs.

The Cap Toe Oxford on the other hand, features a toe-cap, and may involve minimal broguing, making a look that is more grounded, sturdy, and versatile. It may be dressed up in a business suit, or down in relaxed chinos.

The Saddle Oxford takes on the Americana silhouette, devoid of toe-caps and, instead, features a contrasting strip of leather sewn across the top and middle of the shoe down to the sides of the sole. Credited to its originators, the Saddle Oxford may be the perfect pair to wear with your beat-up denim or dress shorts.

The Wingtip Oxford, or Brogues, on the other hand, has the most fun. They have pointed toe-caps with extensions called ‘wingtips’ extending along both sides of the shoes. It features broguing along its edges, and, if you’re lucky, may also come with decorative broguing in the center of the toe cap, called the medallion. One variation of the wingtip is the Spectator, which features two-tone leather that contrasts the toe and heel caps with the uppers, a look favored by jazz musicians and crooners. But for all its fuss and frills, however, the wingtip is not a shoe for strictly formal affairs.

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The Kiltie Oxford is considered the rarest among the lot, and, just like the garment that inspired it—the kilt—may come to odds with our modern idea of masculinity. It features a fringed leather tongue on top hiding the shoelaces in one fell swoop. Yet, for its novelty, it is an ideal pair to complicate an otherwise basic outfit.


Definition: Some can easily confuse a Derby with an Oxford, but to get it right, a Derby, also called the Gibson or Blüchers, has its shoelace eyelets facings stitched on top of the quarters, resulting in an “open lacing” system. You can thank one Prussian army officer named Gebhard Leberecht von Blücher for devising a half boot with two leather flaps to make his standard issue footwear a tad friendlier in the time of the Napoleonic wars. It defined the derby as we know it today, which is a shoe made up of only three pieces: two quarters sewn together on the heel and a plain vamp with a tongue.


Application: But, just like the Oxford, the Derby also comes in the same iterations of plain, cap toe, and wingtip. More casual versions of the Derby come in various colors of leather and suede, and can be worn to complement a sport jacket, a colored inner shirt, or a contrasting pair of chinos or dress shorts. A tough pair of leather Derbies can also be a lifesaver for business attire during inclement weather. But as for the modern-day Prussians of Austria, who wear their Derby proud, a pair of patent leather Derbies is still an undeniable part of their black tie regalia.


Definition: It could as well credit its name to a combination of the words ‘lazy oaf’, but these lace-free slip-on shoes actually trace their history from the moccasins of Native America and the Nordics. They first hit the feet of the elite in 1926 when Raymond Lewis Wildsmith received a commission from King George VI for a country shoe. The result is the 582, now touted as the Wildsmith Loafer, the unlined leather slip-on with reinforced toe box, serrated seam, and a vertical stitching found in its semi-pointed toe.


Application: Since then, various evolutions of the casual shoe followed, like in 1936, when G.H. Bass launched the Wee-Jun, now called the Penny Loafer, due to prep students who would hide pennies under their slotted leather straps, or the Gucci Loafer, whose namesake, Aldo Gucci, adorned it with horse bit hardware in 1953, or the Tasseled Loafer, which Brooks Brothers developed in 1957 to feature leather tassels held in place by straps. But more for its ease than its timelessness, loafers still can’t be considered dress shoes, and are better left with our finest smart casuals.  

Formal Pumps

Definition: The affluent, high-brow cousin to the loafer, the formal pump, also known as the Opera slipper or court shoe, found its first steps in the high-fashion limelight during the Regency period of George IV. Silk-lined and spotlessly shiny, the formal pumps did away with steel cut buckles in favor of the softer grosgrain ribbon at the cap in due course, creating a more streamlined look. And while the rise of the more masculine patent Oxfords replaced the formal pumps in the 19th century, this unassuming hint of nobility to white tie affairs has since reclaimed its rightful place as the most formal of men’s footwear, particularly among the staunchest style arbiters.


Application: To be on the safe side, opt for the patent leather formal pumps to wear with your penguin suits. But a more sinister suede pair can look twice as powerful when worn with a velvet or suede-lined tuxedo.

Monk Straps

Definition: The Monk Strap may be considered a fantastical sartorial choice now, but back in the European Middle Ages, it was more of a practical innovation for Alpine abbey monks, who traded their leather sandals for more altitude-appropriate footwear. Devoid of lacing, the shoe was made up of two quarters and an upper, with a strap to fasten. Due to its early innovation, and its intelligible use of hardware, the monk strap endured to become the perfect choice for moderately formal shoes. Not as uptight as the Oxford or as loose as the Derby, just rightfully, confidently secured.

Application: While its appropriateness for black-tie is still up for debate, a well-polished pair of black single monk strap can offer that needed edge when donning a three-piece suit. Should you require a bit more daring, a brown or tan pair of double monk strap can earn sharp appreciations in a business meeting or a fancy date, worn with the right combination, of, say a navy or gray suit. However, if your pair is in suede, you might have to consider the more relaxed, rugged route.


Chelsea Boot

Definition: Among all of men’s leather footwear, no other shoe experienced more multigenerational swarm status than the Chelsea Boot. Also called the Paddock Boot, the Chelsea had its inception in Victorian England, when the Queen herself commissioned the very first pair of slip-on boots from her royal cobbler, Joseph Sparkes-Hall. Charles Goodyear's development of vulcanized rubber in the 1840s further enhanced the design with the addition of elastic gusset on the sides and the pull tab, enabling the wearer to easily put on and remove the otherwise stubborn boots. So, the fashion caught on like a plague sweeping from the trenches of World War I to the mods of Chelsea’s King’s Road, where it finally earned its iconic name, down to the craggy minimalism of early noughties’ grunge. After all its stylish resurrections, it wouldn’t be smart to be caught without a pair.


Application: While the royals have proven their desirability, the army their durability, the mods their versatility (having worn them with slim suits as well as biker jackets), and grunge gave it street-level authenticity, remember that the Chelsea boot was originally made for the great outdoors and probably shouldn’t be seen worn with a dinner jacket. However, for its sleek sparseness, opt to wear them with your slim-fitting jeans slightly folded in a cuff in celebration of this refined silhouette.

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John Magsaysay
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