Here are five shoes that sport classic, timeless designs, adding a distinguished touch to any man’s ensembles with just the right amount of gravitas.
One’s choice of shoes can make or break an outfit, and this applies in both men and women’s fashion. Though it might seem like women have more options when it comes to shoes, men’s footwear can also be incredibly versatile and stylish—provided that a wearer picks the right pieces for his wardrobe.
As with any good fashion piece, men need trusty pairs of shoes with classic or timeless designs that will look good no matter the occasion. Bonus points if the shoes have a distinguished air to them that embodies quiet luxury.
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If you only have to choose a couple of shoes for your arsenal, below are five particular ones that not only look great with different ensembles, but also show that you’re a man of discerning tastes:
Alden “975 Long Wing Blucher” (in Shell Cordovan)
Originating from Middleborough, Massachusetts, Alden has been making fine shoes since 1884, when it was under the leadership of founder Charles H. Alden. It’s been more than a century since the company’s establishment, yet it continues to expand its offerings and produce high-quality, comfortable dress shoes that exude an old-world elegance.
Among its selections is the “Alden 975 Long Wing Blucher,” fine long wing derby shoes that feature the recognizable dotted patterns that also make them brogues. The pair that comes in Color 8 is particularly stunning, with a deep, rich shade that’s somewhere between black and burgundy.
The shoes feature a barrie last, double leather outsoles, and Goodyear Welt construction (which guarantees they’ll last), and a tempered steel shank under the arch of the foot for maximum support.
For a more luxurious touch, get the shoes made from shell Cordovan, a rare and exquisite equine membrane that tanners can only obtain from a horse’s rump. As such, the material is quite limited for shoemaking, hence its high value. It also requires special creams and products for its upkeep.
However, if one manages to get their hands on Cordovan shoes, they’re certainly worth their weight in gold with their handsome appearance, wrinkle-resistance, water-resistance, and durability.
Gaziano and Girling “St James II”
Enhance your wardrobe with a pair of shoes that the UK’s very own King Charles III favors: the “St James II” by Gaziano and Girling. Tony Gaziano and Dean Girling, the founders of the eponymous brand, have been crafting some of the most distinguished high-end shoes in England for more than two decades. As their official website puts it, the founders take a “zero-compromise” approach to their shoemaking process, ensuring that they only use the best materials and methods they can find.
These include the finest Swiss or French calf leather, oak bark soles, a Goodyear Welt, and Barbour™ threads, which a dedicated and skilled team of around 20 people works on in the brand’s factory in Kettering, Northamptonshire. The result? Inimitable shoes like the St James II, which offer fresh designs that still feel classic and bespoke, melding both Italian comfort and British quality.
Arguably the brand’s most iconic shoe, the St James II features Vintage Cherry Calf leather and a Classic Square TG73 last. The shoes are Oxfords and brogues, sporting the dotted brogue design and the straight, neat cut on the lacing area that makes an Oxford shoe. Contrary to Colin Firth’s Kingsman: The Secret Service line, “Oxfords, not brogues,” both Oxford and Derby shoes can be brogues—as the term “brogue” is simply a way of identifying shoes with perforated patterns.
During King Charles III’s 2023 coronation, Gaziano and Girling even made a pair of bespoke St James shoes for the occasion, a testament to the level of craftsmanship present in their products, making them—quite literally—fit for royals.
John Lobb Paris “City II”
Common in many of the world’s greatest shoemakers is a storied history that culminates in craftsmanship unlike any other. This applies to John Lobb, an English brand that originated in 1866 London and was named after its shoemaker founder. Like Gaziano and Girling, John Lobb has also catered to members of the upper class and royal family, including Edward, Prince of Wales in 1863, writes Sonya Glyn Nicholson for the Parisian Gentleman.
To this day Lobb’s small yet notable London store and workshop still stands, as does the Paris-based store he set up in 1902. People distinguish them as “John Lobb London” and “John Lobb Paris,” respectively, though they do carry a number of differences.
In 1976, the Hermès Group acquired John Lobb Paris, which means its operations and even offerings aren’t the same as those of John Lobb’s original headquarters in London. The main differences being that John Lobb Paris offers ready-to-wear and made-to-order pieces, on top of their bespoke offerings, while John Lobb London only offers bespoke services.
On that note, a must-have pair of John Lobb Paris shoes would be the brand’s “City II,” an Oxford shoe with balanced proportions, a Goodyear Welted construction, and signature twin stitch details. Wear it with business attire, tuxedos, or even jean combos—whatever the occasion, they’re flexible pieces that offer a touch of sophistication to any outfit.
However, if you have a bigger budget, it’s worth getting a pair of bespoke shoes from the legendary John Lobb London, with the shoemaker’s traditional and classic English designs that carry a piece of its long history.
G.H. Bass “Larson Weejuns” Loafer
No shoe collection is complete without some slip-ons, and G.H. Bass’ “Weejuns” loafers for men is a go-top choice for a prep school look. In fact, it was G.H. Bass that first introduced these “Weejuns” penny loafers (named after a front slot that holds a penny) to the world in 1936.
The Weejuns became a landmark shoe for the brand, as well as a staple for the most stylish students in Ivy League schools. Then in 1982, Michael Jackson himself wore a pair of black Weejuns loafers with white socks in his memorable music video for “Thriller,” starting a new craze for the shoes.
Since its establishment in 1876, Bass has upheld its standards for making classy yet functional footwear for all kinds of people, from sportsmen to cultural tastemakers. Its Weejuns capture this perfectly, and are still available today in a wide range of colors and designs. Yet one can never go wrong with the beloved “Larson Weejuns Loafer” in wine, whiskey, or black, with its dressy yet versatile beefroll design and traditional moc stitching.
Berluti “Andy Démesure Leather Loafer”
Another great slip-on, Berluti’s leather loafer is a tribute to artist Andy Warhol, who loved the fashion house’s shoe a great deal. When he had first visited Berluti’s store in 1962, he opted for a pair of leather loafers from Talbinio Berluti—yet his cousin, fellow shoemaker and artist Olga Berluti, had different plans.
She took it upon herself to create a new pair of loafers that used leather from a “subversive” cow that liked scratching itself on barbed wires, hence the large vein that was present in Warhol’s first pair. The artist was so intrigued by the concept that he announced he’d “only want shoes made from the hides of subversive cows,” a move that was avant-garde at the time, and yet the loafer design he came to love ended up becoming a beloved emblem of the brand’s shoemaking heritage.
Today, Berluti still makes the “Andy Démesure Leather Loafer,” a one-piece leather shoe with a hand-stitched apron and backstitching, square tongue, soles and shoe trees with contrasts, and a hand-tooled ‘Berluti’ signature for an elegant finish.
Paradoxically unique yet classic, these shoes make a statement without being too loud, embodying the creative visions of Warhol and an esteemed brand like Berluti.
Banner photo from the Gaziano and Girling website.
