90s Wall Street: three Cuban-heel business shoes to bend the dress code

Last year, I introduced you to a first collaboration with Fratelli Mocchia di Coggiola, this Italo-Parisian tailoring house that captivated me with its ability to handle the codes of masculine elegance with as much rigor as humor. You might remember those tassel loafers and balmoral boots, both featuring a slightly raised Cuban heel that allowed us to play with proportions without falling into caricature.

This new collection, named The Businessman, extends this signature style while setting it in a very particular universe: that of 90s American finance, with just the right amount of tongue-in-cheek humor to avoid taking itself too seriously. We worked on three essential models for the business wardrobe: black cap-toe oxfords, black penny loafers, and my personal favorites, horsebit loafers in a burgundy grained leather.

I. WALL STREET, SMOG, AND CUBAN HEELS

Fratelli Mocchia di Coggiola has built a delightful narrative universe around this collection: Wall Street, with its backdrop of steel, glass, and smog. We meet Luke Stark, a tireless self-made businessman, his ambitious secretary Raph who dreams of overthrowing him, and the mysterious Mr. World, that elusive figure of international finance.

This slightly offbeat staging perfectly reflects the spirit of these shoes: they are perfectly serious in their construction and finishing, but possess that extra soul that distinguishes them from conventional business models. It is precisely this balance that interests me: being within the dress code enough to never make a mistake in a professional context, while retaining that discreet touch of boldness that signals you know your stuff.

II. THE BLACK PENNY LOAFER: FROM NORWEGIAN FJORDS TO WALL STREET

The first model is an extremely classic black box calf penny loafer, typical of the American business world. It could almost be considered austere if we hadn’t integrated the 3.8 cm Cuban heel, which adds a discreet originality that remains professional yet is distinct enough to catch the eye of connoisseurs.

The story of this shoe is worth dwelling on, as it perfectly illustrates how a Norwegian artisanal model became the uniform of Wall Street by way of Ivy League campuses. The entire history of American elegance is played out in this shoe.

When Norwegian Shoemakers Meet Iroquois Moccasins

It all began long before the 1930s, in the Norwegian village of Aurland. As early as 1908, shoemaker Nils Tveranger developed a laceless moccasin that cleverly fused the traditional shoes worn by Scandinavian fishermen with the stitched moccasin toe he had observed among the Iroquois during his apprenticeship in North America. This unexpected encounter between Nordic know-how and Native American technique gave birth to a truly revolutionary model.

The transformation into an American icon occurred in 1936 when G.H. Bass took the concept and created its “Weejun” – a playful contraction of “Norwegian.” Bass’s innovation was the addition of a leather strap with the characteristic diamond-shaped cutout on the vamp, which would become the famous “penny slot,” as well as a “beefroll” stitch on the sides to provide structural support.

Yale, Studied Negligence, and a Coin

The nickname “penny loafer” emerged in the 1950s when Ivy League students started slipping a coin into the diamond slot. As early as 1940, Yale claimed the shoe had “taken the university by storm.” The campus culture of the time favored that famous “studied negligence” and “careful carelessness” that define the preppy style: the penny loafer perfectly met this aspiration, being casual enough for the university spirit while retaining an appropriate elegance.

By the 1980s, the model had become almost a uniform on Wall Street. Black penny loafers were considered perfectly appropriate for business in the United States, widely accepted in business casual settings and even with suits in many industries. Increased security at airports and buildings also played a role: the slip-on design meant no delays at security checks, and for brokers, time is money.

Our Version: Italian Box Calf and a Cuban Heel

The version we offer remains faithful to this American heritage while benefiting from the Spanish craftsmanship that characterizes Fratelli Mocchia di Coggiola’s production. The smooth black leather offers a neat and professional finish, while the strap retains its characteristic diamond cutout. The soft leather interior ensures optimal comfort, even during long days at the office.

The Cuban heel gives the model its distinctive personality. This moderate elevation improves posture and elongates the silhouette without ever being ostentatious. The leather comes from the Italian tannery Conceria Nuova Antilope, in operation since 1958, which produces a box calf recognizable by its chrome tanning and characteristic blue-gray edge.

The penny loafer sits in an interesting area of the formal spectrum: less formal than a lace-up oxford, but dressier than a classic moccasin, especially in its black version. This versatility makes it a particularly valuable model in a contemporary men’s wardrobe where codes have relaxed but not disappeared.

On Wall Street, the black penny loafer would be worn by the confident CEO or VP, the one who has proven himself and negotiates the most strategic deals behind the scenes.

From Rebel to President: James Dean, Elvis, and JFK

James Dean perfectly embodies the penny loafer in “Rebel Without a Cause” and “East of Eden” in 1955, creating that image of youthful sophistication mixed with rebellion that would become iconic. Elvis Presley made them an essential part of his performances, while Michael Jackson immortalized them with his famous white socks to perform the moonwalk in “Billie Jean.”

Beyond the music scene, John F. Kennedy proved that the penny loafer could be truly dressy by wearing it with both suits and casual attire. Miles Davis wore them during recording sessions, confirming their absolute versatility.

How to Wear the Penny Loafer with a Gray Suit

The black penny loafer is a particularly wise choice with the light gray three-piece suit seen in these photos. This combination brilliantly balances professional ambition and measured relaxation: the loafer lightens the rigor of the full suit while maintaining a confident elegance.

The generous opening of the trousers (about 20-21 cm visible here) is crucial for this combination to succeed. This pronounced break on the vamp prevents the loafer from looking too exposed and maintains the formal balance of the outfit. With more fitted trousers, the penny loafer would risk unbalancing the silhouette by appearing too bulky.

With such a light gray, black leather is the obvious choice and maintains the necessary formal anchor. A brown penny loafer, even a dark one, would introduce a too-casual note that would weaken the authority of the ensemble. The black benefits from the structural casualness of the laceless moccasin while preserving the sophistication required for a professional context.

A white poplin or lightweight oxford shirt is the safest choice. The striped burgundy tie seen here works perfectly: it adds a measured color without eccentricity. The three-piece vest cleverly compensates for the casualness introduced by the loafer and reinforces the polished character of the outfit.

The penny loafer is available here for €290 instead of €390

III. The Burgundy Grained Leather Horsebit Loafer: When Florence Arrives on Wall Street

The second model is a horsebit loafer in burgundy grained leather, an emblematic piece that embodies the meeting of Florentine craftsmanship and international elegance. It’s the most ostentatious pair in this collection, but also my favorite: it fully embraces its status while remaining perfectly wearable in a professional context if worn with discernment.

1953: Aldo Gucci Invents the Italian Loafer

The story of this shoe begins precisely in 1953, the year Aldo Gucci opened the brand’s first store outside of Italy, in the lobby of the Savoy-Plaza Hotel in Manhattan. During a previous visit to New York, Aldo had noticed the strong preference of American men for casual slip-on loafers, particularly the Bass Weejuns popular with preppy students.

Consequently, Aldo aimed to create a dressier, more sophisticated Italian version that would appeal to the American clientele while maintaining European refinement. The horsebit detail – that miniature metal ornament consisting of a double ring connected by a bar, inspired by the snaffle bit used in horse harnesses – was added as a tribute to his father Guccio’s fascination with equestrianism.

This equestrian reference is deeply rooted in Gucci’s DNA. Guccio Gucci had worked as a luggage porter at the Savoy Hotel in London after World War I, where he observed wealthy British aristocrats and their lifestyle centered on polo and horse riding. When he founded his company in Florence in 1921, he naturally specialized in high-quality leather goods and equestrian accessories. The horsebit motif had already appeared on Gucci bags in the early 1950s before being incorporated into shoes.

The strategic choice of black leather over brown was decisive: black was not typical for loafers at the time but immediately made them more formal. The metallic horsebit detail added a dressy sophistication that elevated the casual American loafer to something associated with European refinement and status.

From the Jet Set to MoMA: The Consecration of an Icon

Success was instantaneous with the Italian aristocracy and the international jet set. Sophia Loren, Gianni Agnelli (the Italian industrialist and the country’s most important style icon), Cary Grant, Fred Astaire, and Jacqueline Kennedy Onassis quickly adopted the model. In the 1970s, Wall Street businessmen adopted them en masse, earning them the evocative nickname “deal sleds.”

The numbers speak for themselves: by 1969, Gucci was selling 84,000 pairs annually in the United States alone. The ultimate recognition came in 1985 when the Museum of Modern Art in New York added the horsebit loafer to its permanent collection – the only shoe to receive this honor, a testament to its status as an iconic design object beyond its clothing function.

From La Dolce Vita to DiCaprio: A Cinematic Journey

The horsebit loafer has had an impressive film career. Audrey Hepburn dances elegantly in a pair in an iconic scene from “Funny Face” (1957). Sophia Loren wears them in “The Priest’s Wife” (1970), embodying Italian elegance.

On the male side, Dustin Hoffman wears them in “Kramer vs. Kramer” (1979), Matt Damon in “The Talented Mr. Ripley” (1999) – a film regularly cited for its influence on men’s summer wardrobes –, Brad Pitt in “Fight Club” (1999), and Leonardo DiCaprio in “The Wolf of Wall Street” (2013), where Jonah Hill is even seen holding a pair of Gucci loafers.

More recently, the Gucci loafer appeared in “Quantum of Solace” (2008), worn by the villain Dominic Greene, and in “Frost/Nixon” (2008) with Michael Sheen, where the shoe symbolizes a pivotal moment in the life of a former president.

Our Take: Grained Burgundy and Gilt Horsebit

Our choice of burgundy grained leather is a confident statement. Where the classic black version embodies formality and restraint, burgundy adds a welcome touch of personality to an often-monochromatic business wardrobe. The grained leather also comes from Conceria Nuova Antilope: its texture is obtained through a mechanical process where the leather is pressed under different molds to create pronounced grains.

The gilt metal horsebit retains its original shape: the double ring connected by a bar remains immediately recognizable. It’s an ornament that works because it tells a story—that of Florentine equestrian heritage—while remaining discreet enough not to tip into ostentation.

The soft leather interior ensures optimal comfort even on busy days. The Goodyear welt construction guarantees rugged durability and the ability to resole the shoe, significantly extending its lifespan.

How to Avoid the Pitfall of Tastelessness

Born in the Gucci workshops in the mid-20th century, this shoe unabashedly displays its status through the famous gilt metal buckle that adorns the vamp. Yet, when worn with discernment as in these images, it manages to avoid the pitfall of vulgarity to embody a confident elegance.

It is precisely the sobriety of the charcoal gray pinstripe suit that allows the burgundy loafer to express itself without tipping into excess. The fine, tight pinstripes, perfectly vertical, anchor the outfit in a rigorous professional register. The camel coat further tempers the shoe’s boldness: this neutral and timeless color acts as a regulator, a counterweight that prevents the outfit from becoming a gratuitous display.

The burgundy of the loafer dialogues intelligently with the warm tones of the coat while creating sufficient contrast with the cool gray of the suit. This color harmony demonstrates thoughtful consideration: one hasn’t just put on flashy shoes; one has constructed a coherent palette.

The blue and white striped socks, fleetingly visible, confirm this confident approach to the wardrobe. Rather than trying to downplay the impact of the horsebit loafer with discreet accessories, one continues to assert one’s personality in measured touches. The cognac leather briefcase extends this logic: each element of the outfit has its own character while contributing to a remarkably balanced whole.

This outfit is suitable for the accomplished entrepreneur, the creative company director, or the senior consultant who no longer needs to prove his legitimacy and can afford to display a marked personality. The horsebit loafer signals a certain financial confidence and a deep understanding of dress codes: one knows exactly how far one can go without crossing the line.

The burgundy horsebit loafer requires a bit more confidence but offers interesting possibilities. The burgundy color pairs particularly well with shades of gray and navy blue. I would gladly see it with a gray flannel suit or a navy blazer paired with beige wool trousers. In the universe we’ve imagined, this model would perfectly suit the eccentric and bon vivant financier, the one who likes to celebrate his success with a touch of measured extravagance.

Our horsebit loafer is available here for €290 instead of €390 until December 2nd

IV. The Cap-Toe Oxford: From the Oxford Campus to the City of London

Our oxford is for the analyst who works around the clock and wants to climb the ladder at lightning speed: he’s sure not to make a style misstep, but he still wants to maintain a discreet originality with the Cuban heel.

The third model is a cap-toe oxford in smooth black leather. It is the formal shoe par excellence, the culmination of a fascinating evolution that transformed a shoe initially perceived as casual into the ultimate symbol of masculine elegance.

When Oxford Students Invented Rebellion by Foot

The story begins around 1800 with the Oxonian half-boot, which gained popularity among students at the University of Oxford. In 1825, these students shortened the knee-high boots to create the “Oxoniana” – a mid-height boot with buttons, a higher heel than modern oxfords, and a side closure. The first written mention of the “Oxford shoe” dates back to 1846.

The context of this evolution is crucial: the transition occurred as longer trousers with looser cuts replaced the fitted Regency breeches. Men could no longer tuck their trousers into high boots, necessitating shorter footwear. Oxford students, seeking comfort over formality, were pioneers of this change.

Ironically, the Oxonian shoe was initially considered casual – a rebellious choice compared to the formal boots worn by gentlemen. Some men even thought the laces were “too feminine.” Thus, what would become the most formal shoe in the male wardrobe began its career as a symbol of student rebellion.

The Addition of the Cap-Toe: Function and Refinement

The cap-toe variation emerged in the late 19th century with a dual purpose: the extra piece of leather on the toe box served as both reinforcement (protecting the toe area from wear) and aesthetic refinement. This horizontal line across the vamp creates a visual break that slims the shoe’s silhouette.

The cap-toe can be plain-stitched (more formal) or feature perforations along the seam, creating a slightly less formal quarter-brogue. We have chosen the plain version, prioritizing sobriety and formal elegance.

Victorian Consecration and Reign Over the City

In the Victorian era (1837-1901), oxfords began to gain ground beyond the university setting. Their refined appearance made them suitable for formal occasions, aligning perfectly with the era’s emphasis on propriety and decorum. Advances in the Industrial Revolution made quality footwear more accessible to the burgeoning middle class.

In the 20th century, the black cap-toe oxford became the absolute standard for banking, legal, and financial services in the City of London. The “no brown in town” rule made the black oxford an indispensable standard. Before 2016, a report by the UK’s Social Mobility Commission stated: “For men, wearing brown shoes with a business suit is generally considered unacceptable by and for British bankers.”

The typical pre-COVID uniform in the City was a navy suit, a white or blue shirt with silver cufflinks, and black cap-toe oxfords from prestigious makers like Crockett & Jones or Gaziano Girling. Monk straps were explicitly disapproved of. Although dress codes have relaxed since COVID, the black cap-toe oxford remains the safest choice and continues to dominate important client meetings.

Our Version: Classic Rigor and a Cuban Heel

The version we offer scrupulously respects the codes of this historic model. The smooth black leather provides an impeccable and professional finish.

The cap-toe is plain-stitched, without any perforations: we opted for the most formal version possible. The horizontal line across the vamp is perfectly straight and even, a testament to the care taken in its manufacture. This apparent simplicity actually conceals great technical skill: achieving such clean and regular lines requires considerable expertise.

The Goodyear welt construction ensures exceptional durability. This construction method, more costly and technical than the classic Blake stitch, allows the shoe to be resoled multiple times over its life, guaranteeing a lasting investment. The leather sole develops a patina over time and gradually conforms to the shape of the foot, improving comfort with each wear.

The interior is fully lined with soft leather, with no synthetic materials. This attention to invisible details distinguishes quality shoes from industrial models where savings are made on what the eye cannot see.

From Cary Grant to James Bond: British Elegance in Cinema

The black cap-toe oxford is the shoe of cinema’s gentlemen. Cary Grant set the standard in “North by Northwest” (1959), wearing oxblood cap-toe oxfords with a gray Glen plaid suit – the perfect recipe that would inspire James Bond and Don Draper.

Pierce Brosnan and then Daniel Craig in “Skyfall” and “No Time to Die” wear Crockett & Jones Highbury, particularly refined black oxfords. Colin Firth in “Kingsman: The Secret Service” (2015) makes the black cap-toe oxford an essential element of the secret agents’ uniform. Patrick Bateman (Christian Bale) in “American Psycho” (2000) embodies the power and impeccable sophistication of Wall Street.

Maximum Rigor and Discreet Audacity

The black cap-toe oxford sits at the pinnacle of the formal hierarchy in the male wardrobe. Paired here with a navy pinstripe suit, it embodies the archetype of the rigorous businessman: one who masters the codes, respects conventions, and leaves nothing to chance.

The pinstripes, particularly fine and close-set as seen in these photos, immediately evoke the world of finance and consulting. The double-breasted construction further enhances the formal character of the ensemble: the overlapping panels, generous lapels, and high buttoning create an imposing stature that naturally calls for the strictest of oxfords.

The gray herringbone overcoat worn on top extends this structured approach: we remain in an assertive, almost vintage British business register, reminiscent of corporate leaders from the 1950s.

Unlike the brogued toe which allows for some flexibility, or the multi-piece oxford which introduces a bit of lightness, the cap-toe asserts total sobriety. Its clean, straight line unambiguously signals a serious professional positioning. It is the shoe for important transactions, board meetings, and strategic presentations.

This is precisely where the interest of this pair lies: the Cuban heel, slightly raised and curved, adds a unique note without compromising the formality of the ensemble. This technical flourish remains invisible at first glance but subtly alters posture and gait: one gains a few centimeters, the silhouette becomes more elongated.

The green striped socks visible in the close-up confirm this approach: formal codes are scrupulously respected while allowing for measured personal details. This is the elegance of the accomplished professional who no longer needs to prove his legitimacy and can afford these touches of character.

Our black cap-toe oxford is available here for €290 instead of €390

V. The Cuban Heel: From Persian Cavalry to The Beatles

What unites these three models is a particularly successful technical choice: all are Goodyear-welted, ensuring strength, longevity, and the possibility of resoling. A coherent choice for shoes intended for intensive professional use.

The most distinctive element, however, remains the 3.8 cm Cuban heel, slightly angled inward. This type of heel has its roots in the 9th-century Persian cavalry, where it provided stability in the stirrups. After almost disappearing from the male wardrobe in the early 20th century, it was spectacularly reintroduced in October 1961 by The Beatles, who ordered their famous “Beatle Boots” from Anello & Davide in London.

The 1960s-1970s marked the heyday of the Cuban heel. The “Peacock Revolution” legitimized the male heel as a reclamation of a past style, referencing the heels of Louis XIV and the Spanish flamenco tradition. Figures like David Bowie, Elton John, and Prince wore increasingly high heels. Even businessmen adopted slightly higher heels in the 1970s.

After a decline in the 1980s-1990s, the Cuban heel has made a contemporary comeback since the 2000s, notably thanks to Hedi Slimane at Dior Homme and then Saint Laurent. Thus, this detail provides both comfort and a slightly more slender silhouette, without going to excess. This is precisely what gives these models their slightly offbeat character: discreet enough to remain professional, yet distinct enough to stand out.

Production is entrusted to Portuguese workshops renowned for their expertise in manufacturing timeless footwear.

VI. CHOOSING YOUR SIZE

To be as clear as possible: they run large. I personally take one size smaller than usual: where I wear a 41.5 in Crockett & Jones or 7ème Largeur, I took a 40.5 here.

Still, take the time to do the following few measurements; it takes 5 minutes and will prevent 90% of errors.

Length:

• Start by placing a sheet of paper on the floor. Stand on it wearing the socks you plan to use with your future shoes.
• Using a pencil, trace the outline of your foot, keeping the pencil perpendicular.
• Once the outline is done, draw two horizontal marks: one at the heel and the other at the tip of your toes. The distance between these two points will give you the exact length of your foot.

Width:

To get an accurate measurement, first locate the widest part of your foot: it is usually at the metatarsophalangeal joints. Then, wrap your measuring tape around the foot at this precise level, making sure it is horizontal and neither too tight nor too loose.

Size	38.0	38.5	39.0	39.5	40.0	40.5	41.0	41.5	42.0
Length (mm)	238.4	241.7	245.0	248.4	251.7	255.0	258.3	261.7	265.0
Width D (standard)	232.0	234.3	236.5	238.8	241.0	243.3	245.5	247.8	250.0
Width E (wide)	241.0	243.3	245.5	247.8	250.0	252.3	254.5	256.8	259.0
Width EE (extra wide)	245.5	247.8	250.0	252.3	254.5	256.8	259.0	261.3	263.5
Size	42.5	43.0	43.5	44.0	44.5	45.0	45.5	46.0	46.5
Length (mm)	268.3	271.7	275.0	278.3	281.7	285.0	288.3	291.6	295.0
Width D (standard)	252.3	254.5	256.8	259.0	261.3	263.5	265.8	268.0	270.3
Width E (wide)	261.3	263.5	265.8	268.0	270.3	272.5	274.8	277.0	279.3
Width EE (extra wide)	265.8	268.0	270.3	272.5	274.8	277.0	279.3	281.5	283.8
Size	47.0	47.5	48.0	48.5	49.0	49.5	50.0
Length (mm)	298.3	301.6	305.0	308.3	311.6	315.0	318.3
Width D (standard)	272.5	274.8	277.0	279.3	281.5	283.8	286.0
Width E (wide)	281.5	283.8	286.0	288.3	290.5	292.8	295.0
Width EE (extra wide)	286.0	288.3	290.5	292.8	295.0	297.3	299.5

CONCLUSION

This collaboration offers three essential models for the business wardrobe, carefully executed and endowed with a very particular character thanks to the Cuban heel inspired by the 1950s-1970s. These shoes are not mere accessories: they carry within them decades of history, from Ivy League campuses to Wall Street offices, from Milanese runways to cinema screens.

In short, these models are for those who seek shoes that are both sturdy and comfortable, but who also appreciate that extra touch of discreet originality that makes all the difference. A nod to the history of men’s fashion, while remaining resolutely contemporary. Delivery is scheduled for the end of January 2026 as part of a group order.